Potassium Carbonate → HCID 67349861, compound

HRID 910598Notes

Reaction equation

HRID 910598 reaction equation
[CH2:1]([C:8]1[C:9](=[O:18])[NH:10][N:11]([CH:16]=[O:17])[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-].[K+].[K+].[C:25]([O:31][C@@H:32]1[C@@H:37]([O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C@H:36]([O:45][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])[C@@H:35]([CH2:52][O:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[O:34][C@H:33]1Br)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>C(#N)C>[CH2:1]([C:8]1[C:9]([O:18][C@@H:33]2[O:34][C@H:35]([CH2:52][O:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[C@@H:36]([O:45][C:46](=[O:51])[C:47]([CH3:48])([CH3:49])[CH3:50])[C@H:37]([O:38][C:39](=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43])[C@H:32]2[O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:27])[CH3:28])=[N:10][N:11]([CH:16]=[O:17])[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 11430Potassium CarbonateHCID 53466083HCID 53466083, compoundHCID 86628492HCID 86628492, compound

Product 1

HCID 67349861HCID 67349861, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To solution of 4-benzyl-1,2-dihydro-1-formyl-5-isopropyl-3H-pyrazol-3-one (1.07 g) in acetonitrile (20 mL) were added potassium carbonate (0.905 g) and 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl bromide (2.65 g) under stirring at room temperature. In addition, the mixture was heated to 50° C. and stirred for 1 hour. After the reaction completed, the insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1) to give 4-benzyl-1-formyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (1.49 g).

Workup

  1. temperatureIn addition, the mixture was heated to 50° C.
  2. stirringstirred for 1 hour
  3. customthe insoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-42e9e01f17be4f1b9e5ebd913f9bee25
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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