Sodium Hydroxide → 3-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

HRID 7381

Reaction equation

HRID 7381 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([O:7][C@@H:8]2[O:25][C@H:24]([CH2:26][O:27]C(=O)C)[C@@H:19]([O:20]C(=O)C)[C@H:14]([O:15]C(=O)C)[C@H:9]2[O:10]C(=O)C)[C:3]=1[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[CH2:40][CH2:39]2)=[CH:34][CH:33]=1.[OH-].[Na+]>C(O)C>[C@@H:8]1([O:7][C:4]2[C:3]([CH2:31][C:32]3[CH:33]=[CH:34][C:35]([CH:38]4[CH2:40][CH2:39]4)=[CH:36][CH:37]=3)=[C:2]([CH3:1])[NH:6][N:5]=2)[O:25][C@H:24]([CH2:26][OH:27])[C@@H:19]([OH:20])[C@H:14]([OH:15])[C@H:9]1[OH:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 691337285-methyl-4-[(4-cyclopropylphenyl)-methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Product 1

HCID 690132463-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazoleYield 88.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-4-[(4-cyclopropylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.14 g) in ethanol (8.4 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.63 mL), and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (0.087 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=6/1)

Sources & evidence

ORD record
ord-712420777a354dadae1bb00c8c7fe75a
Source dataset
uspto-grants-2006_08
Patent number
US07087579B2

Linked notes

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