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Synlett 2007(10): 1573-1576  
DOI: 10.1055/s-2007-982531
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Mild and Efficient Method for the One-Pot Monocarboxymethylation of Primary Amines

Timothy J. K. Gibbs, Michael Boomhoff, Nicholas C. O. Tomkinson*
School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK
Fax: +44(29)20874030; e-Mail: tomkinsonnc@cardiff.ac.uk;
Further Information

Publication History

Received 23 January 2007
Publication Date:
06 June 2007 (online)

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Abstract

A mild and efficient method for the monocarboxymethylation of primary amines that takes place under aqueous conditions at room temperature is described. Treatment of an aqueous solution of a variety of primary amines with two equivalents of glyoxylic acid leads to the N-formyl glycine derivatives. Direct hydrolysis of the crude reaction solution leads to the products of amine mono­carboxymethylation in good to excellent yield.

Key words

metal-free synthesis - amino acids - glycine derivatives

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6

All compounds prepared were characterised by mp, 1H NMR, 13C NMR, IR, MS and HRMS.