Sodium Methoxide → HCID 68441022, compound

HRID 1592825Notes

Reaction equation

HRID 1592825 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11]([O:22][C@@H:23]3[O:40][C@H:39]([CH2:41][O:42]C(=O)C)[C@@H:34]([O:35]C(=O)C)[C@H:29]([O:30]C(=O)C)[C@H:24]3[O:25]C(=O)C)=[N:12][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]=2[CH3:15])=[CH:5][CH:4]=1.C[O-].[Na+]>CO>[C@@H:23]1([O:22][C:11]2[C:10]([CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[C:14]([CH3:15])[N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=2)[O:40][C@H:39]([CH2:41][OH:42])[C@@H:34]([OH:35])[C@H:29]([OH:30])[C@H:24]1[OH:25]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12993303HCID 12993303, compound

Product 1

HCID 68441022HCID 68441022, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[(4-methoxyphenyl)methyl]-5-methyl-1-phenyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole(0.38 g) in methanol (5 mL) was added sodium methoxide (28% methanol solution, 0.12 mL), 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 column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.32 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-e8c46e8dbc634e1da784af7e90782f32
Source dataset
uspto-grants-2007_11
Patent number
US07294618B2

Reaction notes

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