Preparation of peptides and active esters by a hydrolysis-dehydration reaction with phosphonites, and the application of the reaction to polymer synthesis

Abstract

Dehydration reactions accompanied by hydrolysis of the condensation reagent itself, generalized as “hydrolysis-dehydration,” are seen in the formation of amides and esters using phosphites. The proposed concept was shown to be applicable also to the reactions with other phosphorus compounds, such as phosphinites, phosphonites and phosphonates. Aryl esters of these phosphorus compounds were effective for producing amides and esters, whereas alkyl esters were ineffective. Several peptides and active esters of amino acids were prepared using diphenyl phosphonites in the presence of tertiary amines and extended to the preparation of polypeptides and polyamides. Linear polypeptides and high molecular weight polyamides were obtained by means of diphenyl ethylphosphonite in N-methylpyrrolidone containing pyridine.