A fast procedure for the preparation of amides/peptides from carboxylic acids and azides via two redox reactions: Application to the synthesis of methionine enkephalin

A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction-oxidation (redox) reactions has been described. The primary and secondary amides/peptides are made by using azidotrimethylsilane and alkyl azides/alpha-azido acid derivatives respectively as the direct source of amine components. Benzeneselenol, generated in the reaction medium during carboxyl activation, has been found to be an effective reducing agent for the conversion of azides to primary amines. The methodology has been applied to the synthesis of methionine enkephalin.