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

HRID 33118

Reaction equation

HRID 33118 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:13]([O:18][C@@H:19]3[O:36][C@H:35]([CH2:37][O:38]C(=O)C)[C@@H:30]([O:31]C(=O)C)[C@H:25]([O:26]C(=O)C)[C@H:20]3[O:21]C(=O)C)=[N:14][NH:15][C:16]=2[CH3:17])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C@@H:19]1([O:18][C:13]2[C:12]([CH2:11][C:8]3[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[CH:6][CH:7]=3)=[C:16]([CH3:17])[NH:15][N:14]=2)[O:36][C@H:35]([CH2:37][OH:38])[C@@H:30]([OH:31])[C@H:25]([OH:26])[C@H:20]1[OH:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 673350774-[(4-Isopropoxy-phenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyloxy)-1h-pyrazole

Product 1

HCID 98015583-(beta-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-5-methyl-1H-pyrazoleYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (61 mg) in ethanol (3 mL) was added 1 mol/L aqueous sodium hydroxide solution (0.53 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (39 mg).

Workup

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

Sources & evidence

ORD record
ord-6b58242a1b404f2f95759d9ed5e07d82
Source dataset
uspto-grants-2008_09
Patent number
US07429568B2

Linked notes

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