title: Crystallization-induced chiral inversion as the key step for synthesis of (S)-2-acetylthio-3-phenylpropanoic acid from l-phenylalanine.
abstract: [reaction: see text] A novel crystallization-induced chiral inversion of (S)-2-bromo-3-phenylpropanoic acid to its (R)-enantiomer with excellent enantiomeric excess (96-99%) is achieved. Optically pure (S)-2-acetylthio-3-phenylpropanoic acid can be prepared in good yield from inexpensive and commercially available l-phenylalanine via diazotization/bromination, chiral inversion, and thioacetate substitution reactions.
authors.affiliation: Chemical, Fermentation and Biocatalysis Development Labs, Bristol-Myers Squibb Company, P.O. Box 4755, Syracuse, New York 13221, USA.
authors.forename: Jason G
authors.initials: JG
authors.lastname: Chen
authors.forename: Jingyang
authors.initials: J
authors.lastname: Zhu
authors.forename: Paul M
authors.initials: PM
authors.lastname: Skonezny
authors.forename: Victor
authors.initials: V
authors.lastname: Rosso
authors.forename: John J
authors.initials: JJ
authors.lastname: Venit
mesh_terms: D002384:Catalysis; D003460:Crystallization; D007202:Indicators and Reagents; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry*; D010666:Phenylpropionates / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C503851:2-acetylthio-3-phenylpropanoic acid; D007202:Indicators and Reagents; D010666:Phenylpropionates; D010649:Phenylalanine