Water → (2R)-chloro-3-phenylpropionic acid

Thionyl chloride (0.18 ml, 2.4 mmol) was added dropwise to a solution of 200 mg (1.2 mmol) of (2S)-2-hydroxy-3-phenylpropionic acid (optical purity 100% ee (S)) in 2 ml of dimethoxyethane at room temperature, and the mixture was stirred for 15 hours. To that reaction mixture was added 0.01 ml (0.12 mmol) of pyridine, and the mixture was stirred at 60° C. for 4 hours. Water (10 ml) was added to the reaction mixture and, after 30 minutes of stirring, the mixture was extracted with 50 ml of ethyl acetate. The organic phase was washed with 10 ml of a saturated aqueous solution of sodium chloride and dried over sodium sulfate. The solvent was distilled off under reduced pressure to give 135 mg (yield 61%) of the desired (2R)-2-chloro-3-phenylpropionic acid. The optical purity of the product as determined by the same method as in Example 12 was 97.6% ee (R) (rate of configurational inversion 97.6%).

1. stirringthe mixture was stirred at 60° C. for 4 hours
2. stirringof stirring
3. extractionthe mixture was extracted with 50 ml of ethyl acetate
4. washThe organic phase was washed with 10 ml of a saturated aqueous solution of sodium chloride
5. dry with materialdried over sodium sulfate
6. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-68ea3333903c4a81957930d0868694d9

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07094926B2