Ethyl Acetate → ethyl (3S)-3-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,6-dihydro-2H-pyran-4-carboxylate

HRID 1397202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397202
[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]

Komponenten

6

Edukt 5

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86676959ethyl (3S)-3-{[(2-chloro-4-fluorophenyl)amino]sulfanyl}-3,6-dihydro-2H-pyran-4-carboxylate

Produkt 1

HCID 53344902ethyl (3S)-3-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,6-dihydro-2H-pyran-4-carboxylate

Versuchsvorschrift

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%).

Aufarbeitung

  1. temperaturethe mixture was again cooled to 0° C.
  2. extractionAfter extraction with ethyl acetate (200 mL×2)
  3. washthe extract was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL) and water (200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e1aadf55f2464020a029807ab490d034
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901171B2

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