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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 7
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Original Articles

Simple and Mild One-Pot Synthesis of Dipeptidyl Ureas via Carbamoyl Azides of α-N-Protected Amino Acids

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Pages 1027-1041 | Received 26 Jan 2010, Published online: 03 Mar 2011
 

Abstract

A simple and mild one-pot synthesis of potentially bioactive α-N-protected dipeptidyl ureas is reported. The procedure involves the reaction between the carbamoyl azide of an α-N-protected amino acid and an α-amino acid methyl ester. The reaction is fast (3 h at 45 °C), regardless of the nature of both the reagents, and racemization free. The reported protocol represents a valid alternative to existing methods.

ACKNOWLEDGMENTS

The authors are grateful to Dr. S. Turco for recording 1H and 13C NMR spectra, Dr. I. Duse for MS measurements, and Mr. P. Padovani for expert instrumental maintenance.

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