Efficient One-pot HATU Mediated Coupling of Dicarboxylic Acid and Amines for the Synthesis of Diamide at Ambient Temperature

Title:Efficient One-pot HATU Mediated Coupling of Dicarboxylic Acid and Amines for the Synthesis of Diamide at Ambient Temperature

Volume: 14 Issue: 10

Author(s): Vimal Bhatt*, S. D. Samant and Suhas Pednekar*

Affiliation:

• Department of Chemistry, Ramnarain Ruia College, Matunga, Dadar (E), Mumbai-400019,India

• Department of Chemistry, Ramnarain Ruia College, Matunga, Dadar (E), Mumbai-400019,India

Keywords: Coupling reagents, diamide, HATU, one-pot, peptides, rt.

Abstract: Background: Amide bond is prevalent in peptides. Moreover, at least 25% pharmaceutical products also contain amide bond. A wide ranging strategy including Ugi reaction and related multicomponent reactions is available for the synthesis of amide. While HATU mediated direct one-pot diamide synthesis is scarcely investigated in the literature.

Objective: The objective of this work is to achieve a one pot synthesis of diamide using various coupling reagents.

Method: Straightforward one-pot coupling of dicarboxylic acid with corresponding amine was accomplished in the presence of HATU under ambient condition using 2-Me THF as an industrial green solvent.

Results: A range of (hetero)aromatic and aliphatic dicarboxylic acids were coupled with aromatic and aliphatic amines to give 55-89% yield of the products at ambient temperature.

Conclusion: Among various coupling reagents scrutinized, HATU was proven to be ‘gold standard’ to accomplish one-pot synthesis of diamides.

Cite this article as:

Bhatt Vimal *, Samant D. S. and Pednekar Suhas *, Efficient One-pot HATU Mediated Coupling of Dicarboxylic Acid and Amines for the Synthesis of Diamide at Ambient Temperature, Letters in Organic Chemistry 2017; 14 (10) . https://dx.doi.org/10.2174/1570178614666170710095437