Synthesis of 3-(3-pyridyl)- and 3-(3-benzo[b]thienyl)-D-alanine

• Published in: International journal of peptide and protein research Vol. 29; no. 1; p. 118
• Main Authors: Rao, P N, Burdett, Jr, J E, Cessac, J W, DiNunno, C M, Peterson, D M, Kim, H K
• Format: Journal Article
• Language: English
• Published: Denmark 01.01.1987
• Subjects: Alanine - analogs & derivatives; Alanine - chemical synthesis; Indicators and Reagents; Magnetic Resonance Spectroscopy; Spectrophotometry, Infrared
• ISSN: 0367-8377
• DOI: 10.1111/j.1399-3011.1987.tb02237.x

The DL-arylamino acid ethyl ester derivatives of beta-(3-pyridyl)-DL-alanine, and beta-(3-benzo[b]thienyl)-DL-alanine were synthesized by diethyl acetamidomalonate condensation with the respective arylmethyl halides followed by partial hydrolysis to the monoethyl ester and decarboxylation. Each derivative was enzymatically resolved to a separable mixture of the corresponding N-acetyl-L-amino acid and the unchanged D amino acid derivative. Acidic hydrolysis of the latter gave the corresponding D-amino acid, the optical purity of which was established by HPLC analysis of the 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC) derivative. The free D amino acids were converted to D-BOC derivatives by reaction with di-tert-butyldicarbonate in tert-butyl alcohol, water and sodium hydroxide.