Potassium Carbonate → 4-benzyl-5-isopropyl-1-propionyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 910586Notes

Reaction equation

HRID 910586 reaction equation
[CH2:1]([C:8]1[C:9](=[O:20])[NH:10][N:11]([C:16](=[O:19])[CH2:17][CH3:18])[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:27]([O:33][C@@H:34]1[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:38]([O:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C@@H:37]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[O:36][C@H:35]1Br)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>C(#N)C>[CH2:1]([C:8]1[C:9]([O:20][C@@H:35]2[O:36][C@H:37]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[C@@H:38]([O:47][C:48](=[O:53])[C:49]([CH3:50])([CH3:51])[CH3:52])[C@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C@H:34]2[O:33][C:27](=[O:32])[C:28]([CH3:31])([CH3:29])[CH3:30])=[N:10][N:11]([C:16](=[O:19])[CH2:17][CH3:18])[C:12]=1[CH:13]([CH3:14])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53466083HCID 53466083, compoundHCID 673490834-benzyl-1,2-dihydro-5-isopropyl-1-propionyl-3H-pyrazol-3-one

Product 1

HCID 673487544-benzyl-5-isopropyl-1-propionyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazoleYield 84.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-benzyl-1,2-dihydro-5-isopropyl-1-propionyl-3H-pyrazol-3-one (1.25 g) in acetonitrile (25 mL) were added potassium carbonate (0.951 g) and 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl bromide (2.79 g) under stirring at room temperature. In addition, the mixture was heated to 50° C. and stirred for 3 hours. After the completion of the reaction, 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=20/1) to give 4-benzyl-5-isopropyl-1-propionyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (3.00 g).

Workup

  1. temperatureIn addition, the mixture was heated to 50° C.
  2. stirringstirred for 3 hours
  3. customAfter the completion of the reaction
  4. customthe insoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-37efa0c727604640bceb9bd43560edc9
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

Loading…