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

HRID 910597Notes

Reaction equation

HRID 910597 reaction equation
[CH2:1]([C:8]1[C:9]([O:21][C@@H:22]2[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:23]2[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:10][N:11](C(OCC)=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+].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:1]([C:8]1[C:9]([O:21][C@@H:22]2[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:53])([CH3:55])[CH3:54])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:35])([CH3:37])[CH3:36])[C@H:23]2[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:27])[CH3:28])=[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

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 673506104-benzyl-1-ethoxycarbonyl-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 71.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-1-ethoxycarbonyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (0.15 g) in methanol (3 mL) was added sodium bicarbonate (0.032 g) under stirring at room temperature. The mixture was stirred at room temperature for 12 hours. In addition, to the mixture was added potassium carbonate (0.053 g), and the mixture was stirred for 2 hours. The reaction mixture was poured into water to precipitate the solid. The solids were collected by filtration. The obtained solids 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 (0.098 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. stirringthe mixture was stirred for 2 hours
  3. customto precipitate the solid
  4. filtrationThe solids were collected by filtration
  5. washThe obtained solids were washed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-81865059d8eb4ca181d4e598609cb91b
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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