A mild and efficient method for the one-pot monocarboxymethylation of primary amines

Gibbs, Timothy J. K. and Boomhoff, Michael and Tomkinson, Nicholas C. O. (2007) A mild and efficient method for the one-pot monocarboxymethylation of primary amines. Synlett (10). pp. 1573-1576. ISSN 0936-5214

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Abstract

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