Water → 4-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-tri-fluoromethyl-1H-pyrazole

HRID 1827648

Reaktionsgleichung

Reaktionsgleichung von HRID 1827648
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:19])[NH:12][NH:13][C:14]=2[C:15]([F:18])([F:17])[F:16])=[CH:5][CH:4]=1.[CH3:20][C:21]([O:23][CH2:24][C@H:25]1[O:30][C@H:29](Br)[C@H:28]([O:32][C:33]([CH3:35])=[O:34])[C@@H:27]([O:36][C:37]([CH3:39])=[O:38])[C@@H:26]1[O:40][C:41]([CH3:43])=[O:42])=[O:22].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11]([O:19][C@@H:29]3[O:30][C@H:25]([CH2:24][O:23][C:21](=[O:22])[CH3:20])[C@@H:26]([O:40][C:41](=[O:42])[CH3:43])[C@H:27]([O:36][C:37](=[O:38])[CH3:39])[C@H:28]3[O:32][C:33](=[O:34])[CH3:35])=[N:12][NH:13][C:14]=2[C:15]([F:18])([F:17])[F:16])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 98607281,2-dihydro-4-((4-(methylthio)phenyl)methyl)-5-(trifluoromethyl)-3H-pyrazol-3-one

Produkt 1

HCID 120717124-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-tri-fluoromethyl-1H-pyrazoleAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1,2-dihydro-4-[(4-methylthiophenyl)methyl]-5-trifluoromethyl-3H-pyrazol-3-one (2.0 g) in acetonitrile (100 mL) were added acetobromo-α-D-glucose (3.1 g) and potassium carbonate (1.1 g), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) to give 4-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole (2.0 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-4c3d82f1eb144764ad6afd0eb572487b
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056892B2

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