Tetrahedron letters

Mild one-pot conversion of carboxylic acids to amides or esters with Ph 3 P/trichloroisocyanuric acid

RC Rodrigues, IMA Barros, ELS Lima

Index: Rodrigues, Rogerio Da C.; Barros, Igor M. A.; Lima, Edson L. S. Tetrahedron Letters, 2005 , vol. 46, # 35 p. 5945 - 5947

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Citation Number: 27

Abstract

The reaction of trichloroisocyanuric acid (TCICA) and triphenylphosphine in the presence of a carboxylic acid results in the in situ formation of the corresponding acid chloride under mild conditions. Subsequent addition of amines or alcohols, in the presence of a tertiary amine affords the corresponding amides, or esters, in good to excellent yields. The methodology was applied to the synthesis of a dipeptide.