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

Authors :
Woo, Jacqueline C.S.
Fenster, Erik
Dake, Gregory R.
Source :
Journal of Organic Chemistry. Dec 10, 2004, Vol. 69 Issue 25, 8984-8986
Publication Year :
2004

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. N-methoxy-N-methylmethanesulfonamide, the major byproduct for these reactions, can be removed by placing the product mixture under vacuum for 14-24 hours.

Details

Language :
English
ISSN :
00223263
Volume :
69
Issue :
25
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.126731762