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Synlett 2011(6): 831-833  
DOI: 10.1055/s-0030-1259714
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Unexpected Formation of Tetramethylguanidines by Reaction of Dimethylformamide with Fmoc-Protected Aminoamides

Jacqui F. Young, Neeranat Thienthong, Milton T. W. Hearn, W. Roy Jackson*
Centre for Green Chemistry, Monash University, Clayton, VIC 3800, Australia
Fax: +61(3)99054579; e-Mail: roy.jackson@monash.edu;
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Publication History

Received 21 January 2011
Publication Date:
08 March 2011 (online)

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Abstract

Reactions of primary amines with Fmoc-protected amino acids or Fmoc deprotection of the resulting products in N,N-di­methylformamide gave tetramethylguanidines in variable yields as unexpected by-products.

Key words

guanidine - peptide synthesis - Fmoc protection - Fmoc deprotection - dimethylformamide