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

HRID 33115

反応式

HRID 33115 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 120717124-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-tri-fluoromethyl-1H-pyrazole収率 46.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c0b0124759c844258fcc91bd9de16115
出典データセット
uspto-grants-2008_09
特許番号
US07429568B2

関連ノート

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