Volume 4, Number 1, 53-59, DOI: 10.1007/BF01177509

Reactions of Mercapto amino acids Communication 2. Acylation and alkylation of 3,3-dimethylcysteine

I. L. Knunyants and M. G. Linkova

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Abstract

1.  It has been shown that 3,3-dimethylcysteine is readily acylated by means of acid anhydrides and acid chlorides and that it then forms only N-acyl derivatives.
2.  3,3-Dimethylcysteine is readily alkylated in aqueous alkaline solution, particularly by halogen-substituted acids, with formation of onlyS-alkyl derivatives. With acid chlorides ofbeta-halo carboxylic acids, 3,3-dimethylcysteine forms derivatives of hexahydro-1,4-thiazepin-5-one.
3.  It has been shown that the products of theS-alkylation of 3,3-dimethylcysteine withagr-bromo carboxylic acids are readily converted into derivatives of 3-thiamorpholinone, which is an unusual case of the spontaneous acylation of an amino group by a carboxylic acid.

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