Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent

Abstract

A new synthetic approach for the preparation of amides and peptides containing amino acids as well as aryl acids and amines by employing [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF) as a carboxylic acid activator under mild conditions is delineated. The use of AISF as an acid activator allows the reaction to be performed efficiently. This operationally simple amidation is amenable to a wide variety of carboxylic acids and N^α-protected amino acids. Further, racemization did not occur during the coupling. In addition, a gram-scale reaction is demonstrated.

Key words

[4-(acetylamino)phenyl]imidodisulfuryl difluoride - N^α-protected amino acids - coupling reagent - amides - peptides

Publication History

Received: 16 November 2023

Accepted after revision: 27 December 2023

Article published online:
08 February 2024

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