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

HRID 910599Notes

Reaction equation

HRID 910599 reaction equation
[CH2:1]([C:8]1[C:9]([O:18][C@@H:19]2[O:45][C@H:44]([CH2:46][O:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C@@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[C@H:28]([O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C@H:20]2[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[N:10][N:11](C=O)[C:12]=1[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].O>CO>[CH2:1]([C:8]1[C:9]([O:18][C@@H:19]2[O:45][C@H:44]([CH2:46][O:47][C:48](=[O:53])[C:49]([CH3:50])([CH3:52])[CH3:51])[C@@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[C@H:28]([O:29][C:30](=[O:35])[C:31]([CH3:32])([CH3:34])[CH3:33])[C@H:20]2[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:24])[CH3:25])=[N:10][NH:11][C:12]=1[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 67349861HCID 67349861, compound

Product 1

HCID 673494844-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-betaD-glucopyranosyloxy)-1H-pyrazoleYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-1-formyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.49 g) in methanol (15 mL) was added sodium bicarbonate (0.337 g) under stirring at room temperature. The reaction mixture was stirred at room temperature for 11 hours. After confirming the completion of the reaction, water was added to the mixture 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-glucopyranosyl-oxy)-1H-pyrazole (1.40 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 11 hours
  2. additionwas added to the mixture
  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-1a3e32e0a4a2434994fd5f1edda5836a
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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