Water → HCID 69216629, compound
Reaction equation
O.[CH2:2]([NH:9][CH:10]([C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1)CC(OC)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:25](=[O:28])([O-:27])O.[Na+].[C:30]1(C)C=CC=CC=1>>[CH2:2]([NH:9][C@@H:10]([CH2:16][C:21]1[CH:30]=[CH:17][C:18]2[O:24][CH2:23][O:22][C:19]=2[CH:20]=1)[C:25]([OH:27])=[O:28])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
Conditions
- Temperature
- 30 °C
Procedure
To 37 mL of water were added 7.49 g (23.9 mmol) of methyl (±)-3-benzylamino-3-(3,4-methylenedioxyphenyl)propionate and 1.00 g (12.0 mmol) of sodium hydrogen carbonate, and the mixture was maintained at 30° C. To the resulting mixture was added 37.5 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 24 hours, at the time when the conversion rate of the starting materials reached 29.1%, 40 ml of toluene was added to the reaction mixture. After the resulting mixture was stirred for 15 minutes at room temperature, the mixture was filtered and dried to obtain 1.52 g (Isolated yield based on methyl (±)-3-benzylamino-3-(4-fluorophenyl)propionate=21.2%) of 3-(R) or (S)-benzylamino-3-(3,4-methylenedioxyphenyl)propionic acid as white crystal.
Workup
- additionTo the resulting mixture was added 37.5 mg of lipase (CAL; available from Roche, CHIRAZYME L-2 (trade name))
- customthe mixture was reacted at 30° C.
- additionwas added to the reaction mixture
- stirringAfter the resulting mixture was stirred for 15 minutes at room temperature
- filtrationthe mixture was filtered
- customdried
- customto obtain
Sources & evidence
- ORD record
- ord-295a0f80f66e46bc8c3b2f65a14ff493
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449325B2
Reaction notes
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