Potassium Bicarbonate → HCID 67348403, compound

HRID 910591Notes

Reaction equation

HRID 910591 reaction equation
C([N:4]1[C:8]([CH3:9])=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]([O:17][C@@H:18]2[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@@H:35]([O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[C@H:27]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C@H:19]2[O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[N:5]1)(=O)C.C(=O)(O)[O-].[K+]>CO>[CH2:10]([C:7]1[C:6]([O:17][C@@H:18]2[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@@H:35]([O:36][C:37](=[O:42])[C:38]([CH3:39])([CH3:40])[CH3:41])[C@H:27]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C@H:19]2[O:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:24])[CH3:25])=[N:5][NH:4][C:8]=1[CH3:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 67350156HCID 67350156, compound

Product 1

HCID 67348403HCID 67348403, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-acetyl-4-benzyl-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 (0.058 g) under stirring at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After the precipitation of the crystals by the addition of a solution of glacial acetic acid (0.034 g) in water (20 mL) at room temperature, the mixture was stirred for 2 hours. After the suspension was stirred under ice-cooling for 1 hour, the crystals were collected by filtration. The obtained crystals were washed with a mixed solution of 2-propanol and n-heptane, and dried under reduced pressure to give 4-benzyl-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.90 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. customAfter the precipitation of the crystals
  3. additionby the addition of a solution of glacial acetic acid (0.034 g) in water (20 mL) at room temperature
  4. stirringthe mixture was stirred for 2 hours
  5. stirringAfter the suspension was stirred under ice-
  6. temperaturecooling for 1 hour
  7. filtrationthe crystals were collected by filtration
  8. washThe obtained crystals were washed with a mixed solution of 2-propanol and n-heptane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-9bcace9b8bb64049b9a21d1231133aec
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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