Synthesis of 3‐(3‐pyridyl)‐ and 3‐(3‐benzo[b]thienyl)‐D‐alanine
- 12 January 1987
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 29 (1) , 118-125
- https://doi.org/10.1111/j.1399-3011.1987.tb02237.x
Abstract
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 arlymethyl halides followed by partial hydrolysis to the monoethyl ester and decarboxylation. Each derivative was enzymatically resolved to a separate 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.Keywords
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