The synthesis of D,L p-vinylphenylglycine by amidoalkylation, and its reactions

• Published in: Tetrahedron Vol. 50; no. 23; pp. 7009 - 7018
• Main Authors: SHEFFERDEENOOR, S, BENISHAI, D
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 1994; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; ACID; Dehydrohalogenation; Amidoalkylation; α-Aminoacid; Chemical reactivity; Ethylenic compound
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(01)81353-3

Amidoalkylation of (2-chloroethyl)benzene or (2-bromoethyl)benzene with α-hydroxyhippuric acid and N-methoxycarbonyl α-hydroxyglycine, followed by dehydrohalogenation, affords, N-protected p-vinylphenylglycines. Transformation of the vinyl group leads to N-Methoxycarbonyl- p-[1-(methoxycarbonylamino)ethyl]phenylglycine, N-methoxycarbonyl- p-(epoxyethyl) phenylglycine, N-methoxycarbonyl- p-formyl phenylglycine and N-methoxycarbonyl- p-carboxy phenylglycine. The deprotection of these compounds is described. Amidoalkylation of (2-haloethyl)benzene ( 1a–b) with α-hydroxyhippuric acid and N-methoxycarbonyl α-hydroxyglycine ( 2a-b), followed by dehydrohalogenation, affords N-protected p-vinylphenylglycines ( 5a-b). Transformation of the vinyl group followed by deprotection affords several p-substituted phenylglycines.