Water → 4-benzyl-1-ethoxycarbonyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazole

HRID 910596Notes

Reaction equation

HRID 910596 reaction equation
[CH2:1]([C:8]1[C:9](=[O:21])[NH:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[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:28]([O:34][C@@H:35]1[C@@H:40]([O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[C@H:39]([O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@@H:38]([CH2:55][O:56][C:57](=[O:62])[C:58]([CH3:61])([CH3:60])[CH3:59])[O:37][C@@H:36]1Br)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30].O>C(#N)C>[CH2:1]([C:8]1[C:9]([O:21][C@@H:36]2[O:37][C@H:38]([CH2:55][O:56][C:57](=[O:62])[C:58]([CH3:61])([CH3:60])[CH3:59])[C@@H:39]([O:48][C:49](=[O:54])[C:50]([CH3:51])([CH3:52])[CH3:53])[C@H:40]([O:41][C:42](=[O:47])[C:43]([CH3:44])([CH3:45])[CH3:46])[C@H:35]2[O:34][C:28](=[O:33])[C:29]([CH3:32])([CH3:30])[CH3:31])=[N:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]=1[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10886360((2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl)methyl 2,2-dimethylpropanoateHCID 67349738HCID 67349738, compound

Product 1

HCID 673506104-benzyl-1-ethoxycarbonyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazoleYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-benzyl-1-ethoxycarbonyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (0.100 g) in acetonitrile (3 mL) were added potassium carbonate (0.0575 g) and 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (0.211 g) successively under stirring at room temperature. In addition, the mixture was stirred at 50° C. for 2.5 hours. The mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. 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=1/8 to 1/5 to 1/4) to give 4-benzyl-1-ethoxycarbonyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.15 g).

Workup

  1. stirringIn addition, the mixture was stirred at 50° C. for 2.5 hours
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe insoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/8 to 1/5 to 1/4)

Sources & evidence

ORD record
ord-04ab857bf164438e9bc3d07330bef97c
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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