Hydrochloric Acid → (S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride
Reaction equation
C1(C(=[N:14][C@@H:15]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=2)[C:16]([O:18]C(C)(C)C)=[O:17])C2C=CC=CC=2)C=CC=CC=1.[ClH:35]>>[ClH:35].[NH2:14][C@@H:15]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:28][CH:29]=1)[C:16]([OH:18])=[O:17]Participants
Procedure
A 6 N hydrochloric acid (400 mL) solution of tert-butyl (2S)-2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate (41.2 g, 87.7 mmol) prepared in Reference Example 3 (3a) was heated under reflux for 3 hours and then cooled to room temperature. The reaction solution was concentrated under reduced pressure. The residue was washed with diethyl ether to give 23.8 g of a crude crystal (white powder, yield: 95%, optical purity: 84%). The crude crystalline solid (200 mg) was recrystallized from 1 N hydrochloric acid (1.5 mL) to give 120 mg of the title compound (colorless crystal, yield: 60%). No R-isomer was recognized in this compound by HPLC analysis according to the method described in Reference Example 3 (3c), and thereby it was confirmed that the optical purity was 99% or higher.
Workup
- temperaturewas heated
- temperatureunder reflux for 3 hours
- concentrationThe reaction solution was concentrated under reduced pressure
- washThe residue was washed with diethyl ether
- customto give 23.8 g of a crude crystal (white powder, yield: 95%, optical purity: 84%)
- customThe crude crystalline solid (200 mg) was recrystallized from 1 N hydrochloric acid (1.5 mL)
Sources & evidence
- ORD record
- ord-d6b6bad946cf429190e005d0816592ed
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344029B2
Reaction notes
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