Ethyl Acetate → ethyl (3S)-3-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,6-dihydro-2H-pyran-4-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9]S[C@H]1C(C(OCC)=O)=CCOC1.ClC1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([O:31]O)=O)C=1.[S:33]([O-:36])([O-])=[O:34].[Na+].[Na+].[C:39](=[O:42])([O-])[OH:40].[Na+].[C:44](OCC)(=O)[CH3:45]>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:33]([C@H:25]1[C:26]([C:39]([O:40][CH2:44][CH3:45])=[O:42])=[CH:27][CH2:28][O:31][CH2:29]1)(=[O:36])=[O:34]Participants
Reactant 5
Product 1
Procedure
To a solution (200 mL) of ethyl (3S)-3-{[(2-chloro-4-fluorophenyl)amino]sulfanyl}-3,6-dihydro-2H-pyran-4-carboxylate (12.3 g) in ethyl acetate was added meta-chloroperbenzoic acid (24.5 g) at 0° C. After stirring at room temperature for 2 hr, the mixture was again cooled to 0° C., and 5% aqueous sodium sulfite solution (200 mL) and saturated aqueous sodium hydrogen carbonate solution (200 mL) were added dropwise. After extraction with ethyl acetate (200 mL×2), the extract was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL) and water (200 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=2:1) to give the title compound as a crude product (13.8 g). This product was crystallized from ethyl acetate/diisopropyl ether/hexane (115 mL, 5:100:10) to give the title compound (12.0 g, 90%).
Workup
- temperaturethe mixture was again cooled to 0° C.
- extractionAfter extraction with ethyl acetate (200 mL×2)
- washthe extract was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL) and water (200 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationAfter concentration under reduced pressure
Sources & evidence
- ORD record
- ord-e1aadf55f2464020a029807ab490d034
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901171B2
Reaction notes
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