Water → (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone
Reaction equation
C[O-].[Na+].[F:4][C:5]([F:25])([F:24])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:23])[CH2:14][C@@H:15](OS(C)(=O)=O)[CH2:16][CH3:17])=[CH:8][CH:7]=1.O>O1CCCC1>[CH2:16]([C@H:15]1[N:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]([F:25])([F:24])[F:4])=[CH:7][CH:8]=2)[C:13](=[O:23])[CH2:14]1)[CH3:17]Participants
Procedure
31.8 mg (0.589 mmol) of sodium methoxide was suspended in tetrahydrofuran (1 mL) and a tetrahydrofuran solution (1 mL) containing 200 mg (0.589 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide produced in Example 3 was added dropwise thereto at room temperature for 5 minutes. After stirring at room temperature for further 3.5 hours, water (5 mL) was added and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine and the product was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone as a brown solid (141.6 mg). The reaction yield of the product was determined by HPLC analysis (column; NACALAI COSMO SEAL 5C18-AR packed column 4.6×250 mm: eluent; acetonitrile/5 mM phosphate buffer solution (pH=3)=1/1: flow rate; 1.0 mL/min: column temperature; 30° C: detector; UV 210 nm) to be 60%.
Workup
- additionwas added dropwise
- extractionextraction
- washThe organic layer was washed with saturated brine
- dry with materialthe product was dried with anhydrous sodium sulfate
- customThe solvent was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-ff4afd4afe1c4b3c888029700dece646
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223859B2
Reaction notes
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