Biologically oriented organic sulfur chemistry. 19. Synthesis and properties of 2-amino-5-mercapto-5-methylhexanoic acid, a bishomolog of penicillamine. Use of …

…, L Field, AA Gallo, RJ Gargiulo

Index: Dilbeck; Field; Gallo; Gargiulo Journal of Organic Chemistry, 1978 , vol. 43, # 24 p. 4593 - 4596

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Citation Number: 53

Abstract

Synthesis is reported of 2-amino-5-mercapto-5-methylhexanoic acid (2) as a bishomologue of penicillamine (1). In this synthesis, alkylation of diethyl acetamidomalonate gave ethyl 2- acetamido-2-carbethoxy-5-methyl-4-hexe-noate (4). Addition of a-toluenethiol to 4 using BFrEt20 then gave ethyl 2-acetamido-2-carbethoxy-5-henzy1thio-5-methylhesanoate (6) in 63-74% yield; this reaction appears to he the first use of BFyEt20 as a catalyst for effecting ...