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

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

Journal Name: Letters in Organic Chemistry

Volume 14 , Issue 10 , 2017

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Graphical 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.

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Article Details

Year: 2017
Page: [764 - 768]
Pages: 5
DOI: 10.2174/1570178614666170710095437
Price: $58

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