Water → HCID 69516928、化合物

HRID 1351108ノート

反応式

HRID 1351108 の反応式
[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[OH:25])=[C:16]([CH:26]([CH3:28])[CH3:27])[NH:15][N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[C:29]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39]Br)[CH:34]=1)(=[O:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:29]([O:32][C:33]1[CH:34]=[C:35]([CH:36]=[CH:37][CH:38]=1)[CH2:39][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][C:17]1[C:13]([O:12][C@@H:1]2[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]2[OH:3])=[N:14][NH:15][C:16]=1[CH:26]([CH3:28])[CH3:27])(=[O:31])[CH3:30]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 64220753-(Bromomethyl)phenyl acetateHCID 695165493-(beta-D-glucopyranosyloxy)-4-(2-hydroxybenzyl)-5-isopropyl-1H-pyrazole

生成物 1

HCID 69516928HCID 69516928、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide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. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  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: dichloromethane/methanol=10/1˜5/1)

出典と根拠

ORDレコード
ord-6fcedb9fb67042d9882f3a921a9a145d
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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