Sodium Methoxide → 3-(beta-D-Glucopyranosyloxy)-4-[2-(3-hydroxybenzyloxy)benzyl]-5-isopropyl-1H-pyrazole

HRID 1351109ノート

反応式

HRID 1351109 の反応式
C([O:4][C:5]1[CH:6]=[C:7]([CH:37]=[CH:38][CH:39]=1)[CH2:8][O:9][C:10]1[CH:36]=[CH:35][CH:34]=[CH:33][C:11]=1[CH2:12][C:13]1[C:14]([O:21][C@@H:22]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]2[OH:24])=[N:15][NH:16][C:17]=1[CH:18]([CH3:20])[CH3:19])(=O)C.C[O-].[Na+]>CO>[C@@H:22]1([O:21][C:14]2[C:13]([CH2:12][C:11]3[CH:33]=[CH:34][CH:35]=[CH:36][C:10]=3[O:9][CH2:8][C:7]3[CH:37]=[CH:38][CH:39]=[C:5]([OH:4])[CH:6]=3)=[C:17]([CH:18]([CH3:20])[CH3:19])[NH:16][N:15]=2)[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]1[OH:24]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 695169284-[2-(3-acetyloxybenzyloxy)benzyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

生成物 1

HCID 695161393-(beta-D-Glucopyranosyloxy)-4-[2-(3-hydroxybenzyloxy)benzyl]-5-isopropyl-1H-pyrazole収率 72.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 3-(β-D-glucopyranosyloxy)-4-(2-hydroxybenzyl)-5-isopropyl-1H-pyrazole (150 mg) in N,N-dimethylformamide (1 mL) were added 3-bromomethylphenyl acetate (131 mg) and potassium carbonate (105 mg), and the mixture was stirred at room temperature for 13 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1˜5/1) to give 4-[2-(3-acetyloxybenzyloxy)benzyl]-3-(β-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole. To a solution of 4-[2-(3-acetyloxybenzyloxy)benzyl]-3-(β-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole (12 mg) in methanol (2 mL) was added sodium methoxide (28% methanol solution, 5 μL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (8 mg).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationthe residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

出典と根拠

ORDレコード
ord-23e7b26997e4479aa1cfa3b65574ae5b
出典データセット
uspto-grants-2007_05
特許番号
US07217697B2

反応ノート

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