H. Ottenheijm, A. D. Potman, T. V. Vroonhoven
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
Several S,N-protected-2-mercapto-2-aminopropionic acid derivatives (3a-g Table I) have been prepared by the reaction of thiols with the corresponding N-protected 2-hydroxy-2-amino-propionic acid derivatives 8, prepared from the corresponding amides 7 and pyruvic acid. Recent controversies in the literature regarding this method are discussed. Selective removal of the sulfur-protecting group in 3b and 3e afforded the 2-mercapto-2-acylamidopropionic acids 11, R2 = H and C6H5 respectively. Reaction of 3e with thionyl chloride afforded 4-methyl-4-(acetylthio)-2-phenyl-2-oxazolin-5-one 10. Under these conditions 3g gave the Leuchs' anhydride 14.