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

[ Vol. 14 , Issue. 10 ]

Author(s):

Vimal Bhatt*, S. D. Samant and Suhas Pednekar*   Pages 764 - 768 ( 5 )

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.

Keywords:

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

Affiliation:

Department of Chemistry, Ramnarain Ruia College, Matunga, Dadar (E), Mumbai-400019, Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai-400019, Department of Chemistry, Ramnarain Ruia College, Matunga, Dadar (E), Mumbai-400019

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