A convenient method for the conversion of hindered carboxylic acids to N-methoxy-N-methyl (Weinreb) amides |
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| Authors: | Woo Jacqueline C S Fenster Erik Dake Gregory R |
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| Affiliation: | Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C., Canada V6T 1Z1. |
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| 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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