Tetrahydrofuran → HCID 67034376, compound
Reaction equation
Cl.[NH2:2][C@@H:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:4][OH:5].[OH-].[K+].C1C[O:18][CH2:17]C1.C(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O.C(OCC)(=O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([C@H:3]2[CH2:4][O:5][C:17](=[O:18])[NH:2]2)=[CH:7][CH:8]=1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-2-amino-2-(4-fluorophenyl)ethanol hydrochloride (2.0 g, 10 mmol) in water (50 mL) cooled to 0° C. was added potassium hydroxide (3.5 g, 63 mmol) followed by THF (50 mL) and the reaction was stirred for 20 minutes at 0° C. Bis(trichloromethyl) carbonate (3.1 g, 10 mmol) was added as a solid and the reaction was stirred at 0° C. for 2 hours. The reaction was poured into ethyl acetate (200 mL) and the organic layer was washed with HCl (1N, 30 mL), NaOH (1N, 30 mL) and brine (30 mL), dried over MgSO4 and concentrated under vacuum to give (S)-4-(4-fluorophenyl)oxazolidin-2-one (1 g, 53%).
Workup
- stirringthe reaction was stirred at 0° C. for 2 hours
- washthe organic layer was washed with HCl (1N, 30 mL), NaOH (1N, 30 mL) and brine (30 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-384f5c9a0c2a4c46a9dee3754ebd60fe
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865726B2
Reaction notes
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