Water → 4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-betaD-glucopyranosyloxy)-1H-pyrazole

HRID 910585Notes

Reaction equation

HRID 910585 reaction equation
C([N:4]1[C:8]([CH:9]([CH3:11])[CH3:10])=[C:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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-].[Na+].O>CO>[CH2:12]([C:7]1[C:6]([O:19][C@@H:20]2[O:46][C@H:45]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:51])([CH3:53])[CH3:52])[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]([CH3:33])([CH3:35])[CH3:34])[C@H:21]2[O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:25])[CH3:26])=[N:5][NH:4][C:8]=1[CH:9]([CH3:11])[CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 116147111-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazole

Product 1

HCID 673494844-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-betaD-glucopyranosyloxy)-1H-pyrazoleYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (2.68 g) in methanol (27 mL) was added sodium bicarbonate (0.596 g) under stirring at room temperature. The reaction mixture was stirred at room temperature for 17 hours. After confirming the completion of the reaction, water was added to the reaction mixture in order to precipitate the crystals. The crystals were collected by filtration, and the obtained crystals were washed with water and dried under reduced pressure to give 4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (2.45 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 17 hours
  2. additionwas added to the reaction mixture in order
  3. customto precipitate the crystals
  4. filtrationThe crystals were collected by filtration
  5. washthe obtained crystals were washed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-30d84d97432f4d519dde1b59197fad0a
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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