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A convenient method for the conversion of hindered carboxylic acids to N-methoxy-N-methyl (Weinreb) amides

TitleA convenient method for the conversion of hindered carboxylic acids to N-methoxy-N-methyl (Weinreb) amides
Publication TypeJournal Article
Year of Publication2004
AuthorsWoo, JCS, Fenster, E, Dake, GR
JournalJournal of Organic Chemistry
Volume69
Pagination8984-8986
Date PublishedDec
Type of ArticleArticle
ISBN Number0022-3263
KeywordsCHEMISTRY, CHLORIDE, ESTERIFICATION, ESTERS, GROUP ACTIVATION, lactones, MILD, REAGENT
Abstract

The conversion of sterically hindered carboxylic acids to N-methoxy-N-methyl amides can be efficiently carried out with 1.1 equiv of methanesulfonyl chloride, 3 equiv of triethylamine, and 1.1 equiv of N-methoxy-N-methylamine. Yields for this process range from 59% to 88%. The major byproduct in these reactions, N-methoxy-N-methylmethanesulfonamide, can be removed by placing the product mixture under vacuum for 14-24 h.
URL<Go to ISI>://000225550300061