Method for producing cyanomethyl esters of organic acids, particularly n-acylated amino acids or peptides with configuration retained

摘要

Cyanomethyl esters of carboxylic acids are prepared with retention of configuration by treating the acid with bromoacetonitrile in the presence of a tertiary amine. The process is especially applicable where the carboxylic acid is an N-acylated amino acid or peptide. In a comparative experiment, chloroacetonitrile is employed in place of bromoacetonitrile and gives rise to a product having less retention of configuration. The dipeptide phenylalanine-valine is prepared from the cyanomethyl ester of N-formyl-L-phenylalanine and the tert.butyl ester of L-valine.