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

HRID 457508

Reaction equation

HRID 457508 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-5320544e107e44d09a1b92786ea6b6c4
Source dataset
uspto-grants-2007_03
Patent number
US07189702B2

Linked notes

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