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Amide and Peptide Bond Formation in Water at Room Temperature

Christopher M. Gabriel, Megan Keener, Fabrice Gallou and Bruce H. Lipshutz*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States, Email:

C. M. Gabriel, M. Keener, F. Gallou, B. H. Lipshutz, Org. Lett., 2015, 17, 3968-3971.

DOI: 10.1021/acs.orglett.5b01698


Use of uronium salt (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU) as a coupling reagent, 2,6-lutidine, and TPGS-750-M enables a general, mild, and environmentally responsible method for the formation of amide/peptide bonds in an aqueous micellar medium. The aqueous reaction medium is recyclable leading to low E Factors.

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Key Words

amides, green chemistry

ID: J54-Y2015