Acetic Acid → 4-[(3-fluoro-4-methylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 910593Notes

Reaction equation

HRID 910593 reaction equation
C([N:4]1[C:8]([CH3:9])=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([F:18])[CH:12]=2)[C:6]([O:19][C@@H:20]2[O:46][C@H:45]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@@H:37]([O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C@H:29]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C@H:21]2[O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:5]1)(=O)C.C(=O)(O)[O-].[K+].C(O)(=O)C>CO>[F:18][C:13]1[CH:12]=[C:11]([CH2:10][C:7]2[C:6]([O:19][C@@H:20]3[O:46][C@H:45]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@@H:37]([O:38][C:39](=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43])[C@H:29]([O:30][C:31](=[O:36])[C:32]([CH3:33])([CH3:34])[CH3:35])[C@H:21]3[O:22][C:23](=[O:28])[C:24]([CH3:26])([CH3:27])[CH3:25])=[N:5][NH:4][C:8]=2[CH3:9])[CH:16]=[CH:15][C:14]=1[CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516893Potassium BicarbonateHCID 67350114HCID 67350114, compound

Product 1

HCID 673508054-[(3-fluoro-4-methylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazoleYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-acetyl-4-[(3-fluoro-4-methylphenyl)-methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.75 g) in methanol (5 mL) was added potassium bicarbonate (0.030 g) under stirring at room temperature. The mixture was stirred at 50° C. for 3 hours. To the mixture was added glacial acetic acid (0.022 g) at 60° C., and the resulting mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/5) to give 4-[(3-fluoro-4-methylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.610 g).

Workup

  1. stirringThe mixture was stirred at 50° C. for 3 hours
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-1f081f51230e49a996f9baa2dc7e914a
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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