Water → HCID 69218632, compound

Participants

Reaction Conditions

Reaction Steps

To 4 mL of water were added 400 mg (1.28 mmol) of methyl (±)-3-benzylamino-3-(3,4-methylenedioxyphenyl)propionate and 107 mg (1.28 mmol) of sodium hydrogen carbonate, and the mixture was maintained to 30° C. To the resulting mixture was added 2 mg of lipase (CAL; available from Roche, CHIRAZYME L-2 (trade name)) originated from Candida antarctica at the same temperature, and the mixture was reacted at 30° C. while stirring. After 20 hours, at the time when the conversion rate of the starting materials reached 46.2%, 8 ml of ethyl acetate and 112 mg of sodium hydrogen carbonate were added to the reaction mixture and the aqueous layer was extracted. The resulting aqueous layer was adjusted to an inner pH of 2.0 with 2 mol/L of hydrochloric acid aqueous solution, and 8 ml of ethyl acetate and 500 mg of sodium chloride were added to the mixture to extract the organic layer. The resulting organic layer was dried over magnesium sulfate, filtered and concentrated to obtain 135 mg (Isolated yield based on methyl (±)-3-benzylamino-3-(4-fluorophenyl)propionate=35.3%) of (R) or (S)-3-benzylamino-3-(3,4-methylenedioxyphenyl)propionic acid as white crystal.

Provenance & Evidence