Literature DB >> 15575791

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

Jacqueline C S Woo1, Erik Fenster, Gregory R Dake.   

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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Year:  2004        PMID: 15575791     DOI: 10.1021/jo048385h

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Simple Synthesis of Amides and Weinreb Amides via Use of PPh3 or Polymer-Supported PPh3 and Iodine.

Authors:  Amit Kumar; Hari Kiran Akula; Mahesh K Lakshman
Journal:  European J Org Chem       Date:  2010-05

2.  A complex stereochemical relay approach to the antimalarial alkaloid ocimicide A1. Evidence for a structural revision.

Authors:  Herman Nikolayevskiy; Maung Kyaw Moe Tun; Paul R Rablen; Choukri Ben Mamoun; Seth B Herzon
Journal:  Chem Sci       Date:  2017-05-04       Impact factor: 9.825

  2 in total

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