Water → HCID 69219589, compound
Reaction equation
O.[CH2:2]([NH:9][CH:10]([C:16]1[CH:21]=[CH:20][C:19](C)=[CH:18][CH:17]=1)CC(OC)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:23](=[O:26])([O-])[OH:24].[Na+].[C:28]1(C)C=CC=C[CH:29]=1>>[CH2:10]([NH:9][C@@H:2]([CH2:3][C:8]1[CH:7]=[CH:6][C:5]([CH3:4])=[CH:29][CH:28]=1)[C:23]([OH:24])=[O:26])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
Conditions
- Temperature
- 30 °C
Procedure
To 372 mL of water were added 37.20 g (0.13 mol) of methyl (±)-3-benzylamino-3-(p-tolyl)propionate and 11.03 g (0.13 mol) of sodium hydrogen carbonate, and the mixture was maintained at 30° C. To the resulting mixture was added 186 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 8.5 hours, at the time when the conversion rate of the starting materials reached 39.4%, the reaction mixture was filtered to obtain a solid state product. To the resulting product was added 200 ml of toluene and the mixture was stirred at room temperature for 2 hours, then, filtered and dried to obtain 11.11 g (Isolated yield based on methyl (±)-3-benzylamino-3-(4-fluorophenyl)propionate=31.4%) of 3-(R) or (S)-benzylamino-3-(p-tolyl)propionic acid as white crystal.
Workup
- additionTo the resulting mixture was added 186 mg of lipase (CAL; available from Roche, CHIRAZYME L-2 (trade name))
- customthe mixture was reacted at 30° C.
- filtrationthe reaction mixture was filtered
- customto obtain a solid state product
- stirringthe mixture was stirred at room temperature for 2 hours
- filtrationfiltered
- customdried
- customto obtain
Sources & evidence
- ORD record
- ord-1798fb825fdd447391f7423a0b49d604
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449325B2
Reaction notes
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