Potassium Carbonate → HCID 67350156, compound

HRID 910588Notes

Reaction equation

HRID 910588 reaction equation
[C:1]([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])[NH:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:25]1(Br)[O:51][C@H:50]([CH2:52][O:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[C@@H:42]([O:43][C:44](=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46])[C@H:34]([O:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[C@H:26]1[O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>C(#N)C.O1CCCC1>[C:1]([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:25]2[O:51][C@H:50]([CH2:52][O:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[C@@H:42]([O:43][C:44](=[O:49])[C:45]([CH3:46])([CH3:47])[CH3:48])[C@H:34]([O:35][C:36](=[O:41])[C:37]([CH3:38])([CH3:39])[CH3:40])[C@H:26]2[O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:30])[CH3:31])=[N:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67349091HCID 67349091, compoundHCID 67351373HCID 67351373, compound

Product 1

HCID 67350156HCID 67350156, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-acetyl-4-benzyl-1,2-dihydro-5-methyl-3H-pyrazol-3-one (0.75 g) in acetonitrile (5 mL) and tetrahydrofuran (3 mL) was added potassium carbonate (0.675 g) under stirring at room temperature. After the mixture was stirred at 50° C. for 1 hour, 1-bromo-2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (2.27 g) was added to the mixture. The mixture was stirred at 50° C. for 6 hours. 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: ethyl acetate/n-hexane=1/10 to 1/5) to give 1-acetyl-4-benzyl-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.88 g).

Workup

  1. stirringAfter the mixture was stirred at 50° C. for 1 hour
  2. stirringThe mixture was stirred at 50° C. for 6 hours
  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: ethyl acetate/n-hexane=1/10 to 1/5)

Sources & evidence

ORD record
ord-2168c392acc9438fa726f48f9d6d58e0
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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