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A Convenient Method for the Conversion of Hindered Carboxylic Acids to N-Methoxy-N-methyl (Weinreb) Amides

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Jacqueline C. S. Woo, Erik Fenster, and Gregory R. Dake*

Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C., Canada, V6T 1Z1 gdake@chem.ubc.ca

J. Org. Chem., 2004, 69 (25), pp 8984–8986

DOI: 10.1021/jo048385h

Publication Date (Web): November 9, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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.

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Published In Issue December 10, 2004
Received September 13, 2004

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Note

A Convenient Method for the Conversion of Hindered Carboxylic Acids to N-Methoxy-N-methyl (Weinreb) Amides

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

An Easy and Convenient Synthesis of Weinreb Amides and Hydroxamates

A One-Flask Synthesis of Weinreb Amides from Chiral and Achiral Carboxylic Acids Using the Deoxo-Fluor Fluorinating Reagent

Direct Conversion of N-Methoxy-N-methylamides (Weinreb Amides) to Ketones via a Nonclassical Wittig Reaction

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