Crystallization-induced chiral inversion as the key step for synthesis of (S)-2-acetylthio-3-phenylpropanoic acid from l-phenylalanine.
[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.
Chen
Jason G
JG
Chemical, Fermentation and Biocatalysis Development Labs, Bristol-Myers Squibb Company, P.O. Box 4755, Syracuse, New York 13221, USA.
Zhu
Jingyang
J
Skonezny
Paul M
PM
Rosso
Victor
V
Venit
John J
JJ
D002384:Catalysis; D003460:Crystallization; D007202:Indicators and Reagents; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry*; D010666:Phenylpropionates / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
C503851:2-acetylthio-3-phenylpropanoic acid; D007202:Indicators and Reagents; D010666:Phenylpropionates; D010649:Phenylalanine