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Synthesis 2004(1): 37-42  
DOI: 10.1055/s-2003-44374
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reagents for Efficient Conversion of Amines to Protected Guanidines

Tomasz Gers, Danuta Kunce, Paweł Markowski, Jan Izdebski*
Laboratory of Peptides, Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
Fax: +48(22)8225996; e-Mail: izdebski@chem.uw.edu.pl;
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Publication History

Received 16 June 2003
Publication Date:
09 December 2003 (online)

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Abstract

Two new guanidinylation reagents, N,N′-bis(ortho-chloro-Cbz)-S-methylisothiourea and N,N′-bis(ortho-bromo-Cbz)-S-methylisothiourea, were compared with the already known N,N′-bis(Boc)-S-methylisothiourea and N,N′-bis(Cbz)-S-methylisothiourea. The new reagents proved to be superior to the known reagents. The reactions with all the new reagents were accelerated by addition of DMAP. N,N′-Bis(ortho-chloro-Cbz)- and N,N′-bis(ortho-bromo-Cbz)guanidines are stable when treated with trifluoroacetic acid and can be converted to guanidines by hydrogenolysis.

Key words

guanidine - guanidinylation - guanylation - isothiourea - protecting groups