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

HRID 910592Notes

Reaction equation

HRID 910592 reaction equation
C([N:4]1[C:8]([CH3:9])=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[C:6]([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:5]1)(=O)C.C(=O)(O)[O-].[K+].C(O)(=O)C>CO.O>[CH:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][C:7]2[C:6]([O:21][C@@H:22]3[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]3[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:5][NH:4][C:8]=2[CH3:9])=[CH:16][CH:15]=1)([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516893Potassium BicarbonateHCID 673498631-acetyl-4-[(4-isopropoxyphenyl)-methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Product 1

HCID 673510654-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazoleYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-acetyl-4-[(4-isopropoxyphenyl)-methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.00 g) in methanol (10 mL) was added potassium bicarbonate (0.038 g) under stirring at room temperature. The suspension turned into a solution by heating to reflux, and the mixture was stirred for further 2 hours. After confirming the completion of the reaction, a solution of glacial acetic acid (0.022 g) in water (10 mL) was added to the mixture at 60° C. to precipitate the crystals. The suspension was cooled to room temperature, and stirred under ice-cooling for 1 hour. The crystals were collected by filtration, and the obtained crystals were washed with a mixed solution of 2-propanol and n-heptane, and dried under reduced pressure to give 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.890 g).

Workup

  1. temperatureby heating
  2. temperatureto reflux
  3. stirringthe mixture was stirred for further 2 hours
  4. customthe completion of the reaction
  5. customto precipitate the crystals
  6. temperatureThe suspension was cooled to room temperature
  7. stirringstirred under ice-
  8. temperaturecooling for 1 hour
  9. filtrationThe crystals were collected by filtration
  10. washthe obtained crystals were washed with a mixed solution of 2-propanol and n-heptane
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-c37590eece334a808da1f3619d5977a7
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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