Synthesis 2006(3): 455-460  
DOI: 10.1055/s-2006-926273
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Applications of β-Aminoethanesulfonyl Azides

Arwin J. Brouwer, Remco Merkx, Katarzyna Dabrowska, Dirk T. S. Rijkers, Rob M. J. Liskamp*
Department of Medicinal Chemistry, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The Netherlands
Fax: +31(30)2536655; e-Mail: R.M.J.Liskamp@pharm.uu.nl;
Further Information

Publication History

Received 15 July 2005
Publication Date:
11 January 2006 (online)

Abstract

A very efficient method for the synthesis of β-amino­ethanesulfonyl azides is descibed. These aliphatic sulfonyl azides are accessible starting from a variety of protected amino acids, including those having functionalized side chains. Furthermore, these sulfonyl azides can be coupled to thio acids, and can be substituted with different aliphatic amines.

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In the NMR spectra, also broad, low-intensity signals were observed, presumably due to the presence of the minor Fmoc rotamer.