Acylation of Amino Acids with Furancarboxylic Acid Chlorides

Abstract

Acylation of aromatic amino acids with furancarboxylic acid chlorides effectively proceeds in water-acetone medium at pH 8-9. Aliphatic amino acids are acylated at higher pH values, but under these conditions hydrolysis of acid chlorides becomes the main process. Acylation of chlorohydrates of methyl esters of aliphatic amino acids proceeds smoothly in chloroform in the presence of triethylamine. Alkaline hydrolysis of obtained products leads to N-acylated amino acids containing furan heteroring in the acyl radical.