Water → HCID 69516407, compound

HRID 1351105Notes

Reaction equation

HRID 1351105 reaction equation
[OH:1][C:2]1[CH:43]=[CH:42][CH:41]=[CH:40][C:3]=1[CH2:4][C:5]1[C:6]([O:16][C@@H:17]2[O:34][C@H:33]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[C@@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]2[O:19][C:20](=[O:22])[CH3:21])=[N:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]=1[CH:10]([CH3:12])[CH3:11].[CH2:44](Br)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:44]([O:1][C:2]1[CH:43]=[CH:42][CH:41]=[CH:40][C:3]=1[CH2:4][C:5]1[C:6]([O:16][C@@H:17]2[O:34][C@H:33]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[C@@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]2[O:19][C:20](=[O:22])[CH3:21])=[N:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]=1[CH:10]([CH3:12])[CH3:11])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69516736HCID 69516736, compound

Product 1

HCID 69516407HCID 69516407, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-hydroxybenzyl)-1-(2-hydroxyethyl)-5-isopropyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (35 mg) in N,N-dimethylformamide (3 mL) were added benzyl bromide (20 mg) and potassium carbonate (18 mg), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/3—ethyl acetate) to give 4-(2-benzyloxybenzyl)-1-(2-hydroxyethyl)-5-isopropyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (33 mg). To a solution of 4-(2-benzyloxybenzyl)-1-(2-hydroxyethyl)-5-isopropyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (33 mg) in methanol (3 mL) was added sodium methoxide (28% methanol solution, 9 μL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (20 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/3—ethyl acetate)

Sources & evidence

ORD record
ord-a5aabaa237e8484a8c3c6f0742451c48
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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