Sodium Methoxide → HCID 69014017, compound

HRID 457509Notes

Reaction equation

HRID 457509 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:13]([O:21][C@@H:22]3[O:39][C@H:38]([CH2:40][O:41]C(=O)C)[C@@H:33]([O:34]C(=O)C)[C@H:28]([O:29]C(=O)C)[C@H:23]3[O:24]C(=O)C)=[N:14][NH:15][C:16]=2[C:17]([F:20])([F:19])[F:18])=[CH:7][CH:6]=1.C[O-].[Na+]>CO>[C@@H:22]1([O:21][C:13]2[C:12]([CH2:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:10][CH:9]=3)=[C:16]([C:17]([F:20])([F:19])[F:18])[NH:15][N:14]=2)[O:39][C@H:38]([CH2:40][OH:41])[C@@H:33]([OH:34])[C@H:28]([OH:29])[C@H:23]1[OH:24]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 691344624-{[4-(3-hydroxypropyl)phenyl]methyl}-5-trifluoromethyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Product 1

HCID 69014017HCID 69014017, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{[4-(3-hydroxypropyl)phenyl]methyl}-5-trifluoromethyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.45 g) in methanol (7 mL) was added sodium methoxide (28% methanol solution, 0.068 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give 3-(β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropyl)phenyl]methyl}-5-trifluoromethyl-1H-pyrazole (0.17 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=6/1)

Sources & evidence

ORD record
ord-ccc3d49f04de4335ab65f477829f0108
Source dataset
uspto-grants-2007_03
Patent number
US07189702B2

Reaction notes

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