Reaction Attempts Edition1 (2010-04-27)

8/9/2019 Reaction Attempts Edition1 (2010-04-27)

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Reaction AttemptsThe UsefulChem Project

Compiled and Performed by:

Jean-Claude Bradley, Khalid Mirza, and Andrew Lang

with

Tim Bohinski, David Bulger, Alicia Merchant, Emily Messner, Marshall Moritz, Shannon Oseback, Rikesh Parikh, Mitesh Shah

Version: April 28, 2010

Licensed under a Creative Commons Attribution 2.5 License

Data is available as CC0

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PrefaceReaction Attempts First Edition

Data Source: the UsefulChem project

Introduction

Open Notebook Science (ONS) refers to the practice of making the full contents of a laboratory notebook and all associated raw data files available innear real time.[1] This represents an opportunity for everyone to benefit from work in progress in an open research group. However, in order to makeuse of the information, it must be easily discoverable. A simple strategy to increase discoverability is redundancy over multiple communicationplatforms.

In another project - the Open Notebook Science Solubility Challenge[2] - we published non-aqueous solubility data in the form of physical anddownloadable (PDF) books.[3] Although it is possible to search the solubility database using web query interfaces, exploration of a GoogleSpreadsheet, an XML feed, etc.[4], having a physical copy in the laboratory has proved to be very convenient in several instances. A similar formatfor reactions will also be useful.

The UsefulChem Project

UsefulChem started in 2005 as an organic chemistry Open Notebook Science project with a main goal of discovering new anti-malarial agents that canbe prepared by simple and cheap syntheses.[5] Most of the reactions on UsefuChem are Ugi reactions, which involve the mixing of an amine,aldehyde, carboxylic acid and isonitrile in a solvent at room temperature generally for a few hours to days.[6] The multicomponent design of the Ugireaction and the simple reaction conditions make it ideal for exploring large virtual libraries and selecting compounds of interest to make.[7]

Isolation of the Ugi products can be immensely simpler, cheaper and readily scalable if they precipitate in pure form from the reaction mixture. Tothis end, much of the research in the UsefulChem project focuses on reaction conditions that lead to this outcome.[8] This is in fact the origin of theONS Solubility Challenge discussed above.[9]

The Reaction Attempts Database

In order to look for patterns in the reaction conditions which led to Ugi product precipitation, the CombiUgiResults Google Spreadsheet was setup.[10] Reactions indexed there can be sorted by precipitation outcome, solvent, reactant, concentration, etc. and links to the laboratory notebookpages can be followed for full details. However, this sheet is designed specifically for Ugi reactions and contains columns specifically for thealdehyde, amine, carboxylic acid and isonitrile.

In order to enable the tracking of other types of reactions, the information in the CombiUgiResults sheet was reformatted into two other sheets:ReactionAttempts[11] (containing reagents and reactants) and RXIDsReactionAttempts[12] (containing reaction conditions and results, such assolvent, concentration of limiting reactant, appearance of a precipitate, yield, etc.). The two sheets are connected via the use of a common ReactionID.This format permits the representation of any type of reaction, with an unlimited number of reactants and products.[13]

By definition, any Open Notebook Science project in a work in progress. The listing of a reaction in this database only means that the researcherattempted or is in the process of attempting it. Whatever the situation, a link to the laboratory notebook page is provided, where the most recentinformation is available. The philosophy used here is that partial information is always better than no information at all. Thus a researcherinvestigating the prior use a particular reactant in a Ugi reaction might find the report that a precipitate was obtained in methanol helpful for designingtheir own reactions, even if the characterization of the precipitate is still pending. At the very least, knowing that a certain researcher has at leastattempted a similar reaction is enough information for initiating a discussion, which may lead to valuable insights.

Reaction Attempts on Chemspider

Although SMILES[14] are provided in the spreadsheets, the primary key to identify compounds is the ChemSpider ID (CSID)[15]. This allows us torender molecule images in the book automatically. In the case of the ONS Solubility Challenge book[3], use of the CSID enables a convenient way tocalculate various descriptors for displaying values in the book.

In addition, the compounds in the Reaction Attempts database are indexed on ChemSpider as two Data Sources: ReactantsAttemptedReactions andProductsAttemptedReactions[13]. In this way a substructure search for either reactants or products will identify indexed molecules. Clicking on the

Syntheses tab in the ChemSpider record for a selected molecule will then reveal a list of hyperlinks to the relevant laboratory notebook pages.

Organization of the Book

In keeping with the layout of the ONS Solubility Challenge Book, the reactants are listed in alphabetical order. Each entry displays the list of reactionswhere the reactant was used. This includes a scheme with all reactants and product as well as key metadata: the researcher, reaction type, solvent,limiting reactant concentration, observation of a precipitate, comments and a reference (links to the laboratory notebook page).

In this edition, only Ugi reactions are included. The reaction schemes are laid out in the following order: carboxylic acid, amine, aldehyde andisonitrile. This should allow for easy comparison between schemes within a given record. Reactions where the Ugi product was isolated andcharacterized are marked with a green check and the percent yield is noted. Since the Ugi products do not have simple common names, they are notincluded as separate entries. However, all reactions where the synthesis of a specific Ugi product was attempted can be found by looking up theentries for any of the four reactants.

Although this compilation is not exhaustive, it does cover the vast majority of reactions in the UsefulChem project to date. Future editions will includeother reactions from UsefulChem and other sources.

Archive

This edition is linked to the UsefulChem interactive data archive (ZIP)[16], (DVD)[17], ReactionAttempts (XLS)[18] andRXIDsReactionAttempts(XLS)[19] taken on 2010-04-27.

References

1. Open Notebook Science Wikipedia Entry http://en.wikipedia.org/wiki/Open_Notebook_Science2. Open Notebook Science Solubility Challenge Wiki http://onschallenge.wikispaces.com3. Bradley, J.-C. First Edition of ONS Solubility Challenge Book UsefulChem Blog (2009)

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http://en.wikipedia.org/wiki/Open_Notebook_Sciencehttp://onschallenge.wikispaces.com/http://onschallenge.wikispaces.com/http://en.wikipedia.org/wiki/Open_Notebook_Science


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http://usefulchem.blogspot.com/2009/12/first-edition-of-ons-solubility.htm l4. Open Notebook Science Solubility Challenge List of Experiments page http://onschallenge.wikispaces.com/list+of+experiments5. UsefulChem Wiki http://usefulchem.wikispaces.com6. Ugi Reaction Wikipedia Entry http://en.wikipedia.org/wiki/Ugi_reaction7. Dmling, A., & Ugi, I. (2000). Multicomponent Reactions with Isocyanides. Angewandte Chemie International English Edition, 39(18), 3168-3210.doi: 10.1002/1521-3773(20000915)39:183.0.CO;2-U.8. UsefulChem List of Experiments http://usefulchem.wikispaces.com/All+Reactions9. Bradley, J.-C. Open Notebook Science Challenge UsefulChem Blog (2008)http://usefulchem.blogspot.com/2008/09/open-notebook-science-challenge.html10. CombiUgiResults Google Spreadsheet http://spreadsheets.google.com/ccc?key=plwwufp30hfpUERhse9y5Kw11. ReactionAttempts Google Spreadsheethttp://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdG9NejNLcDNUMkVBVURGM01TR0NxdXc12. RXIDsReactionAttempts Google Spreadsheethttp://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdGVENVFMWjdzaGd2REJTTnA4RG5vblE13. Bradley, J.-C. Reaction Attempts on ChemSpider UsefulChem Blog (2010)http://usefulchem.blogspot.com/2010/03/reaction-attempts-on-chemspider.html14. SMILES Wikipedia Entry http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification15. ChemSpider Web Site http://www.chemspider.com/16. UC archive Drexel server (ZIP) http://showme.physics.drexel.edu/usefulchem/archives/usefulchem2010-04-27.zip17. UC archive on lulu.com (DVD) http://www.lulu.com/product/dvd/usefulchem-archive/1079184718. Bradley, J.-C.; Lang, A.. Reaction Attempts Reactants and Products. UsefulChem. 2010-04-27.URL:http://spreadsheets.google.com/pub?key=toMz3Kp3T2EAUDF3MSGCquw&output=xls. Accessed: 2010-04-27.(Archived by WebCite at http://www.webcitation.org/5pIsFEbT9)19. Bradley, J.-C.; Lang, A.. Reaction Attempts RXIDs. UsefulChem. 2010-04-27.URL:http://spreadsheets.google.com/pub?key=teD5QLZ7shgvDBSNp8DnonQ&output=xls. Accessed: 2010-04-27.(Archived by WebCite at http://www.webcitation.org/5pIs2eh62)

Reactions

1-aminocyclohexane-1-carboxylic acid

Reaction ID UCEXP233-1

Researcher David Bulger

Reaction Type Ugi

Solvent methanol

Limiting Reactant 0.921 M

Precipitate No

Comments -

Reference http://usefulchem.wikispaces.com/Exp233

+ + +


benzylamine 3,5-dimethoxybenzaldehyde t-butyl isocyanide 24534439



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +


benzylamine 3,5-dimethoxybenzaldehyde cyclohexylisocyanide 24534440



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -

3
http://usefulchem.blogspot.com/2009/12/first-edition-of-ons-solubility.htmlhttp://onschallenge.wikispaces.com/list+of+experimentshttp://onschallenge.wikispaces.com/list+of+experimentshttp://usefulchem.wikispaces.com/http://en.wikipedia.org/wiki/Ugi_reactionhttp://en.wikipedia.org/wiki/Ugi_reactionhttp://usefulchem.wikispaces.com/All+Reactionshttp://usefulchem.blogspot.com/2008/09/open-notebook-science-challenge.htmlhttp://spreadsheets.google.com/ccc?key=plwwufp30hfpUERhse9y5Kwhttp://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdG9NejNLcDNUMkVBVURGM01TR0NxdXchttp://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdGVENVFMWjdzaGd2REJTTnA4RG5vblEhttp://usefulchem.blogspot.com/2010/03/reaction-attempts-on-chemspider.htmlhttp://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificationhttp://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificationhttp://www.chemspider.com/http://showme.physics.drexel.edu/usefulchem/archives/usefulchem2010-04-27.ziphttp://showme.physics.drexel.edu/usefulchem/archives/usefulchem2010-04-27.ziphttp://www.lulu.com/product/dvd/usefulchem-archive/10791847http://spreadsheets.google.com/pub?key=toMz3Kp3T2EAUDF3MSGCquw&output=xlshttp://www.webcitation.org/5pIsFEbT9http://spreadsheets.google.com/pub?key=toMz3Kp3T2EAUDF3MSGCquw&output=xlshttp://www.webcitation.org/5pIsFEbT9http://spreadsheets.google.com/pub?key=teD5QLZ7shgvDBSNp8DnonQ&output=xlshttp://spreadsheets.google.com/pub?key=teD5QLZ7shgvDBSNp8DnonQ&output=xlshttp://www.webcitation.org/5pIs2eh62http://usefulchem.wikispaces.com/Exp233http://usefulchem.wikispaces.com/Exp233http://usefulchem.wikispaces.com/Exp233http://usefulchem.wikispaces.com/Exp233http://www.webcitation.org/5pIs2eh62http://spreadsheets.google.com/pub?key=teD5QLZ7shgvDBSNp8DnonQ&output=xlshttp://www.webcitation.org/5pIsFEbT9http://spreadsheets.google.com/pub?key=toMz3Kp3T2EAUDF3MSGCquw&output=xlshttp://www.lulu.com/product/dvd/usefulchem-archive/10791847http://showme.physics.drexel.edu/usefulchem/archives/usefulchem2010-04-27.ziphttp://www.chemspider.com/http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificationhttp://usefulchem.blogspot.com/2010/03/reaction-attempts-on-chemspider.htmlhttp://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdGVENVFMWjdzaGd2REJTTnA4RG5vblEhttp://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdG9NejNLcDNUMkVBVURGM01TR0NxdXchttp://spreadsheets.google.com/ccc?key=plwwufp30hfpUERhse9y5Kwhttp://usefulchem.blogspot.com/2008/09/open-notebook-science-challenge.htmlhttp://usefulchem.wikispaces.com/All+Reactionshttp://en.wikipedia.org/wiki/Ugi_reactionhttp://usefulchem.wikispaces.com/http://onschallenge.wikispaces.com/list+of+experimentshttp://usefulchem.blogspot.com/2009/12/first-edition-of-ons-solubility.html


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+ + +

1-aminocyclohexane-1-carboxylic acid benzylamine 3,5-dimethoxybenzaldehyde t-butyl isocyanide 24534439



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +


benzylamine 3,5-dimethoxybenzaldehyde cyclohexylisocyanide 24534440

1-heptylamine


Researcher Rikesh Parikh

Reaction Type Ugi

Solvent methanol


Precipitate No

Comments Protocol from Explan005 followed


+ + +

Boc-Trp-OH 1-heptylamine o-vanillin benzyl isocyanide 21106061



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-heptylamine o-vanillin n-butyl isocyanide 21106065



Reaction Type Ugi

Solvent methanol

4
http://usefulchem.wikispaces.com/Exp233http://usefulchem.wikispaces.com/Exp233http://usefulchem.wikispaces.com/Exp131http://usefulchem.wikispaces.com/Exp131http://usefulchem.wikispaces.com/Exp131http://usefulchem.wikispaces.com/Exp131http://usefulchem.wikispaces.com/Exp233http://usefulchem.wikispaces.com/Exp233


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Precipitate No



+ + +

Boc-Trp-OH 1-heptylamine o-vanillin 1-pentyl isocyanide 21106066

Reaction ID UCEXP148A-V1B153

Researcher Khalid Mirza/ Emily Messner

Reaction Type Ugi

Solvent methanol


Precipitate Yes but the aldehyde alone is not soluble in methanol

Yield 50.1 %



+ + +

crotonic acid 1-heptylamine phenanthrene-9-carboxaldehyde t -butyl isocyanide 21106058

Reaction ID UCEXP180

Researcher Shannon Oseback

Reaction Type Ugi

Solvent methanol


Precipitate no and aldehyde alone not solube



+ + +

acetic acid 1-heptylamine phenanthrene-9-carboxaldehyde n-butyl isocyanide 21105834

Reaction ID UCEXP182Researcher Emily Messner

Reaction Type Ugi

Solvent methanol


Precipitate Reactants Insoluble

Comments -


+ + +

furoic acid 1-heptylamine phenanthrene-9-carboxaldehyde n-butyl isocyanide 21168529

Reaction ID UCEXP215A

Researcher Khalid Mirza

Reaction Type Ugi

Solvent THF


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Precipitate No

Comments -


+ + +




Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

glycolic acid 1-heptylamine 2-methoxy-1-naphthaldehyde tosylmethyl isocyanide 24528188

Reaction ID UCExp236-15


Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

3,3'-dichloropivalic acid 1-heptylamine 4-(trifluoromethyl)benzaldehyde t-butyl isocyanide 24528288



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

crotonic acid 1-heptylamine phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528310



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -

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+ + +




Reaction Type Ugi

Solvent THF


Precipitate Yes

Product Awaiting Characterization

Comments -


+ + +

Boc-Gly-OH 1-heptylamine phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528332



Reaction Type Ugi

Solvent THF


Precipitate Yes


Comments -


+ + +

Boc-Gly-OH 1-heptylamine phenanthrene-9-carboxaldehyde t -butyl isocyanide 24528344



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

3,4-methylenedioxyphenylacetic

acid1-heptylamine 4-(trifluoromethyl)benzaldehyde n-butyl isocyanide 24528377



Reaction Type Ugi

Solvent methanol


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Precipitate No

Comments -


+ + +


acid1-heptylamine 4-(trifluoromethyl)benzaldehyde t-butyl isocyanide 24528380

1-hexylamine



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

formic acid 1-hexylamine 2-naphthaldehyde 1-pentyl isocyanide 21106078



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-hexylamine o-vanillin n-butyl isocyanide 21106063



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-hexylamine o-vanillin 1-pentyl isocyanide 21106064

Reaction ID UCEXP181-064V2


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Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

3-methylbut-2-enoic acid 1-hexylamine 3,4-dihydroxybenzaldehyde tosylmethyl isocyanide 24528103



Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid 1-hexylamine 2-hydroxybenzaldehyde t -butyl isocyanide 24528114



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

4-hydroxybenzoic acid 1-hexylamine 3-methoxybenzaldehyde tosylmethyl isocyanide 24528139



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-hexylamine benzaldehyde n-butyl isocyanide 24528183



Reaction Type Ugi

Solvent methanol

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Precipitate Yes

Yield - %

Comments -


+ + +

3,3'-dichloropivalic acid 1-hexylamine 4-(trifluoromethyl)benzaldehyde t-butyl isocyanide 24528280



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

methacrylic acid 1-hexylamine 4-(trifluoromethyl)benzaldehyde t-butyl isocyanide 24528301



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

crotonic acid 1-hexylamine phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528311



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

crotonic acid 1-hexylamine phenanthrene-9-carboxaldehyde t -butyl isocyanide 24528321



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Reaction Type Ugi

Solvent THF


Precipitate Yes


Comments -


+ + +

Boc-Gly-OH 1-hexylamine phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528333



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +


acid1-hexylamine 4-(trifluoromethyl)benzaldehyde n-butyl isocyanide 24528366

1-octylamine



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-octylamine o-vanillin benzyl isocyanide 21106062



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments Protocol from Explan005 followedReference http://usefulchem.wikispaces.com/Exp134

+ + +

Boc-Trp-OH 1-octylamine o-vanillin n-butyl isocyanide 21106072

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Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-octylamine o-vanillin 1-pentyl isocyanide 21106073

1-pentyl isocyanide

Reaction ID UCEXP130-2Researcher Rikesh Parikh

Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

formic acid 1-hexylamine 2-naphthaldehyde 1-pentyl isocyanide 21106078



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH furfurylamine veratraldehyde 1-pentyl isocyanide 21106068



Reaction Type Ugi

Solvent methanol


Precipitate NoComments Protocol from Explan005 followed


+ + +

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Boc-Trp -OH 5- methylfurfurylamine veratraldehyde 1-pentyl isocyanide 21106069



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-hexylamine o-vanillin 1-pentyl isocyanide 21106064



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-heptylamine o-vanillin 1-pentyl isocyanide 21106066



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-propylamine o-vanillin 1-pentyl isocyanide 21106071



Reaction Type Ugi

Solvent methanol


Precipitate No



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+ + +

Boc-Trp-OH 1-octylamine o-vanillin 1-pentyl isocyanide 21106073



Reaction Type Ugi

Solvent methanol


Precipitate Yes

Product Pending

Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid


+ + +

Boc-Gly-OH furfurylamine piperonal 1-pentyl isocyanide 24528159



Reaction Type Ugi

Solvent THF


Precipitate No

Comments 0.5 mmol of isocyanide was added to 900uL of a 0.55M solution of aldehyde; amine and acid


+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde 1-pentyl isocyanide 24528167



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid furfurylamine piperonal 1-pentyl isocyanide 24528175

Reaction ID UCEXP232-03Researcher Khalid Mirza

Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


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+ + +

Boc-Gly-OH furfurylamine benzaldehyde 1-pentyl isocyanide 24528190



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 4- methylbenzaldehyde 1- pentyl isocyanide 24528195



Reaction Type Ugi

Solvent methanol


Precipitate Yes

Product Pending

Comments -


+ + +

Boc-Gly-OH furfurylamine 4-(trifluoromethyl)benzaldehyde 1-pentyl isocyanide 24528200



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine crotonaldehyde 1-pentyl isocyanide 24528204


Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


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+ + +

Boc-Gly-OH furfurylamine diphenylacetaldehyde 1- pentyl isocyanide 24528209



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine cyclohexancarboxaldehyde 1-pentyl isocyanide 24528214



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2-furaldehyde 1-pentyl isocyanide 24528219



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2- hydroxybenzaldehyde 1- pentyl isocyanide 24528224



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


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+ + +

Boc-Gly-OH furfurylamine o-tolualdehyde 1-pentyl isocyanide 24528229



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 4- methoxybenzaldehyde 1-pentyl isocyanide 24528234



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine hexanaldehyde 1-pentyl isocyanide 24528239



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine trans-2-hexenal 1-pentyl isocyanide 24528243



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


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+ + +

Boc-Gly-OH furfurylamine 2-phenylpropionaldehyde 1-pentyl isocyanide 24534418



Reaction Type Ugi

Solvent methanol


Precipitate Yes

Product Pending

Comments -


+ + +

Boc-Gly-OH furfurylamine m-anisaldehyde 1-pentyl isocyanide 24528253



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2- ethylbutyraldehyde 1-pentyl isocyanide 24528258



Reaction Type Ugi

Solvent THF


Precipitate Yes

Yield - %

Comments -


+ + +

phenylacetic acid furfurylamine phenanthrene-9-carboxaldehyde 1-pentyl isocyanide 24528347



Reaction Type Ugi

Solvent THF


Precipitate Yes but 48h

Comments -


18


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+ + +

phenylacetic acid 5-methylfurfurylamine phenanthrene-9-carboxaldehyde 1-pentyl isocyanide 24528351



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +


acidmethylamine veratraldehyde 1-pentyl isocyanide 24528358



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +


acidmethylamine veratraldehyde 1-pentyl isocyanide 24528358


Researcher Marshall Moritz

Reaction Type Ugi

Solvent benzene


Precipitate No

Comments -


+ + +

phenylacetic acid 5-methylfurfurylamine phenanthrene-9-carboxaldehyde 1-pentyl isocyanide 24528382



Reaction Type Ugi

Solvent benzene


Precipitate No

Comments -

19
http://usefulchem.wikispaces.com/Exp241http://usefulchem.wikispaces.com/Exp241http://usefulchem.wikispaces.com/Exp242http://usefulchem.wikispaces.com/Exp242http://usefulchem.wikispaces.com/Exp241http://usefulchem.wikispaces.com/Exp241


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+ + +

phenylacetic acid furfurylamine phenanthrene-9-carboxaldehyde 1-pentyl isocyanide 24528386

1-propylamine



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-propylamine o-vanillin n-butyl isocyanide 21106070



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

Boc-Trp-OH 1-propylamine o-vanillin 1-pentyl isocyanide 21106071

Reaction ID UCEXP167A-V1B12

Researcher Tim Bohinsky

Reaction Type Ugi

Solvent methanol





+ + +


acid1-propylamine phenanthrene-9-carboxaldehyde n-butyl isocyanide 21105597

Reaction ID UCEXP174G/V2B39


Reaction Type Ugi

Solvent methanol

20


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Precipitate No



+ + +

3,4-dihydroxyphenylaceticacid

1-propylamine 4-methylbenzaldehyde tosylmethyl isocyanide 21106199

Reaction ID UCEXP177

Researcher Shannon Oseback

Reaction Type Ugi

Solvent methanol





+ + +

phenylacetic acid 1-propylamine phenanthrene-9-carboxaldehyde n-butyl isocyanide 21105831



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +


1-propylamine 2-hydroxybenzaldehyde tosylmethyl isocyanide 24528102



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

diphenylacetic acid 1-propylamine 3,4-dihydroxybenzaldehyde n-butyl isocyanide 24528112



Reaction Type Ugi

Solvent methanol

21


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Precipitate No

Comments -


+ + +

3,3'-dichloropivalic acid 1-propylamine 4-(trifluoromethyl)benzaldehyde n-butyl isocyanide 24528286



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

crotonic acid 1-propylamine phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528313



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

crotonic acid 1-propylamine phenanthrene-9-carboxaldehyde t -butyl isocyanide 24528323



Reaction Type Ugi

Solvent THF


Precipitate Yes


Comments -


+ + +

Boc-Gly-OH 1-propylamine phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528335



Reaction Type Ugi

Solvent methanol


22


23/581

Precipitate No

Comments -


+ + +


acid1-propylamine 2,4-dimethylbenzaldehyde t-butyl isocyanide 24528375

1-pyrenebutyric acid

Reaction ID UCEXP147-3V2B6

Researcher Mitesh Shah

Reaction Type Ugi

Solvent methanol


Precipitate No


Reference http://usefulchem.wikispaces.com/Exp+147

+ + +

1- pyrenebutyric acid methylamine 2- naphthaldehyde t- butyl isocyanide 21105841

Reaction ID UCEXP171B/V2B2


Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine o-vanillin t-butyl isocyanide 21106056

Reaction ID UCEXP171D/V2B4


Reaction Type Ugi

Solvent methanol


Precipitate Yes

Product No



+ + +

1-pyrenebutyric acid benzylamine o-vanillin t-butyl isocyanide 21105846

Reaction ID UCEXP171FV2B6

23
http://usefulchem.wikispaces.com/Exp241http://usefulchem.wikispaces.com/Exp+147http://usefulchem.wikispaces.com/Exp171http://usefulchem.wikispaces.com/Exp171http://usefulchem.wikispaces.com/Exp171http://usefulchem.wikispaces.com/Exp171http://usefulchem.wikispaces.com/Exp+147http://usefulchem.wikispaces.com/Exp241


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Reaction Type Ugi

Solvent methanol


Precipitate Yes but reactants initially insoluble

Yield - %



+ + +


Reaction ID UCEXP171KV2B11


Reaction Type Ugi

Solvent methanol


Precipitate Yes

Yield - %



+ + +

1-pyrenebutyric acid methylamine 4-(dimethylamino)benzaldehyde t-butyl isocyanide 21105842

Reaction ID UCEXP171LV2B-12Researcher Khalid Mirza

Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid methylamine phenanthrene-9-carboxaldehyde t-butyl isocyanide 21106039

Reaction ID UCEXP173B/V2B14


Reaction Type Ugi

Solvent methanol


Precipitate Yes but reactants initially insoluble

Yield - %



+ + +

1-pyrenebutyric acid methylamine 4-methylbenzaldehyde t -butyl isocyanide 21105844

24


25/581

Reaction ID UCEXP173C/V2B15


Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid methylamine 4-(trifluoromethyl)benzaldehyde t-butyl isocyanide 21106044

Reaction ID UCEXP173D/V2B16


Reaction Type Ugi

Solvent methanol

Limiting Reactant 0.224 MPrecipitate Reactants Insoluble



+ + +

1-pyrenebutyric acid methylamine 2-hydroxybenzaldehyde n-butyl isocyanide 21106048

Reaction ID UCEXP173J/V2B22Researcher Khalid Mirza

Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid methylamine 3,4-dihydroxybenzaldehyde t-butyl isocyanide 21106038

Reaction ID UCEXP173P/V2B28


Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid methylamine 3-methoxybenzaldehyde t -butyl isocyanide 21106050


25


26/581


Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid 3-chloroaniline 2-methylbenzaldehyde n-butyl isocyanide 24528530



Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid 1-hexylamine 2-hydroxybenzaldehyde t -butyl isocyanide 24528114



Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid aniline benzaldehyde n-butyl isocyanide 21106208



Reaction Type Ugi

Solvent methanol





+ + +

1-pyrenebutyric acid methylamine 2,4-dimethylbenzaldehyde t -butyl isocyanide 21106206

Reaction ID UCEXP215C


Reaction Type Ugi

26


27/581

Solvent THF


Precipitate No

Comments -


+ + +


Reaction ID UCEXP215D


Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +




Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +




Reaction Type Ugi

Solvent THF


27


28/581

Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde t -butyl isocyanide 24528165



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde n-butyl isocyanide 24528166



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde 1-pentyl isocyanide 24528167



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde cyclohexylisocyanide 24528168



Reaction Type Ugi

Solvent THF


Precipitate No


28


29/581


+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde benzyl isocyanide 24528169



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde tosylmethyl isocyanide 24528170



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde2-morpholinoethyl

isocyanide24528171



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde2-chloro-6-

methylphenylisocyanide

24528172



Reaction Type Ugi

Solvent THF


Precipitate No

29


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+ + +

1-pyrenebutyric acid furfurylamine piperonal t-butyl isocyanide 24528173



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid furfurylamine piperonal n-butyl isocyanide 24528174



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid furfurylamine piperonal 1-pentyl isocyanide 24528175



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid furfurylamine piperonal cyclohexylisocyanide 24528176



Reaction Type Ugi

Solvent THF


Precipitate No



30
http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227http://usefulchem.wikispaces.com/Exp227


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+ + +

1-pyrenebutyric acid furfurylamine piperonal benzyl isocyanide 24528177



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1- pyrenebutyric acid furfurylamine piperonal tosylmethyl isocyanide 24528178



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid furfurylamine piperonal2-morpholinoethyl

isocyanide24528179



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid furfurylamine piperonal2-chloro-6-


24528180



Reaction Type Ugi

Solvent THF


Precipitate No



31


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+ + +




Reaction Type Ugi

Solvent THF


Precipitate No



+ + +




Reaction Type Ugi

Solvent THF


Precipitate Yes

Product Pending



+ + +

1- pyrenebutyric acid furfurylamine 2- furaldehyde n- butyl isocyanide 24528187

1,1,3,3-tetramethylbutyl isocyanide



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine benzaldehyde1,1,3,3-

tetramethylbutylisocyanide

24528192



Reaction Type Ugi

Solvent methanol

32


33/581


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 4- methylbenzaldehyde1,1,3,3-


24528197



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 4-(trifluoromethyl)benzaldehyde1,1,3,3-


24528201


Researcher Khalid MirzaReaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine crotonaldehyde1,1,3,3-


24528206



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine diphenylacetaldehyde1,1,3,3-


24528211

33


34/581



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine cyclohexancarboxaldehyde1,1,3,3-


24528216



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2-furaldehyde

1,1,3,3-


24528221



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2- hydroxybenzaldehyde1,1,3,3-


24528226



Reaction Type Ugi

Solvent methanol


Precipitate Yes

Product Pending

Comments -


+ + +

34


35/581

Boc-Gly-OH furfurylamine o-tolualdehyde1,1,3,3-

tetramethylbutyl

isocyanide

24528231



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 4- methoxybenzaldehyde1,1,3,3-


24528236



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine hexanaldehyde1,1,3,3-


24528241


Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine trans-2-hexenal1,1,3,3-


24528245



Reaction Type Ugi

35


36/581

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2- phenylpropionaldehyde1,1,3,3-


24534420



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -Reference http://usefulchem.wikispaces.com/Exp232

+ + +

Boc-Gly-OH furfurylamine m-anisaldehyde1,1,3,3-


24528255



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2- ethylbutyraldehyde1,1,3,3-


24528260



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

phenylacetic acid furfurylamine phenanthrene-9-carboxaldehyde1,1,3,3-


21782583

36


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38/581

phenylacetic acid furfurylamine phenanthrene-9-carboxaldehyde1,1,3,3-

tetramethylbutyl

isocyanide

24528385



Reaction Type Ugi

Solvent benzene


Precipitate No

Comments -


+ + +

phenylacetic acid 5-methylfurfurylamine phenanthrene-9-carboxaldehyde1,1,3,3-


24528390



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +


acidfurfurylamine piperonal

1,1,3,3-tetramethylbutyl

isocyanide24528395

Reaction ID UCExp245-10Researcher Khalid Mirza

Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +




isocyanide24528395



Reaction Type Ugi

38


39/581

Solvent methanol


Precipitate No

Comments -


+ + +


acid5-methylfurfurylamine piperonal


isocyanide24528398



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -Reference http://usefulchem.wikispaces.com/Exp245

+ + +


acid5-methylfurfurylamine piperonal


isocyanide24528398



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

cbz-proline furfurylamine piperonal1,1,3,3-


24528403



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

cbz-proline furfurylamine piperonal1,1,3,3-


24528403

39


40/581



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

cbz-proline 5-methylfurfurylamine piperonal1,1,3,3-


24528405



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

cbz-proline 5-methylfurfurylamine piperonal1,1,3,3-


24528405



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +




isocyanide24528408



Reaction Type Ugi

Solvent methanol

Limiting Reactant 0.683 MPrecipitate No

Comments -


+ + +

40


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acid

furfurylamine piperonal1,1,3,3-

tetramethylbutyl

isocyanide

24528408

2-chloro-6-methylphenyl isocyanide



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid


+ + +

Boc-Gly-OH furfurylamine piperonal2-chloro-6-


24528164



Reaction Type UgiSolvent THF


Precipitate No



+ + +

1-pyrenebutyric acid 5-methylfurfurylamine benzaldehyde

2-chloro-6-


24528172



Reaction Type Ugi

Solvent THF


Precipitate No



+ + +

1-pyrenebutyric acid furfurylamine piperonal2-chloro-6-


24528180

41


42/581

2-chloroaniline

Reaction ID UCEXP173N/V2B26


Reaction Type Ugi

Solvent methanol


Precipitate Reactants InsolubleComments Protocol from Explan005 followed


+ + +

decanoic acid 2-chloroaniline o-vanillin tosylmethyl isocyanide 21105847


Researcher Khalid MirzaReaction Type Ugi

Solvent methanol





+ + +


2-chloroaniline 2-naphthaldehyde t-butyl isocyanide 24528117



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

decanoic acid 2-chloroaniline 3-methoxybenzaldehyde tosylmethyl isocyanide 24528124



Reaction Type Ugi

Solvent methanol


Precipitate No



+ + +

42


43/581

4-hydroxybenzoic acid 2-chloroaniline 4-methoxybenzaldehyde tosylmethyl isocyanide 24528130



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments Protocol from Explan005 followedReference http://usefulchem.wikispaces.com/Exp181

+ + +

4-hydroxybenzoic acid 2-chloroaniline veratraldehyde tosylmethyl isocyanide 24534443



Reaction Type UgiSolvent methanol


Precipitate No

Comments -


+ + +

3,3'-dichloropivalic acid 2-chloroaniline 4-(trifluoromethyl)benzaldehyde t-butyl isocyanide 24528282



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

crotonic acid 2-chloroaniline phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528303



Reaction Type Ugi

Solvent THF


Precipitate No

Comments -


+ + +

crotonic acid 2-chloroaniline phenanthrene-9-carboxaldehyde t -butyl isocyanide 24528315

43


44/581



Reaction Type Ugi

Solvent THF


Precipitate Yes


Comments -


+ + +

Boc-Gly-OH 2-chloroaniline phenanthrene-9-carboxaldehyde cyclohexylisocyanide 24528325



Reaction Type Ugi

Solvent THFLimiting Reactant 1.718 M

Precipitate Yes but solvent evaporated

Comments -


+ + +

Boc-Gly-OH 2-chloroaniline phenanthrene-9-carboxaldehyde t -butyl isocyanide 24528337



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +


acid2-chloroaniline 4-(trifluoromethyl)benzaldehyde n-butyl isocyanide 24528368

2-ethylbutyraldehyde



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

44


45/581

Boc-Gly-OH furfurylamine 2-ethylbutyraldehyde t-butyl isocyanide 24528256



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2-ethylbutyraldehyde n-butyl isocyanide 24528257



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2- ethylbutyraldehyde 1-pentyl isocyanide 24528258



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2- ethylbutyraldehyde cyclohexylisocyanide 24528259



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


45


46/581

+ + +

Boc-Gly-OH furfurylamine 2- ethylbutyraldehyde1,1,3,3-

tetramethylbutyl

isocyanide

24528260

2-furaldehyde



Reaction Type Ugi

Solvent THF


Precipitate Yes

Product Pending



+ + +

1- pyrenebutyric acid furfurylamine 2- furaldehyde n- butyl isocyanide 24528187



Reaction Type Ugi

Solvent methanol


Precipitate Yes

Product Pending

Comments -


+ + +

Boc-Gly-OH furfurylamine 2-furaldehyde t-butyl isocyanide 24528217



Reaction Type Ugi

Solvent methanol


Precipitate No

Comments -


+ + +

Boc-Gly-OH furfurylamine 2-furaldehyde n-butyl isocyanide 24528218



Reaction Type Ugi

46

8/9/201

Documents

Reaction Attempts Edition1 (2010-04-27)