Sodium Methoxide → Sergliflozin

HRID 985379Notes

Reaction equation

HRID 985379 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:29]([O:30]C(=O)C)[C@H:28]([O:34]C(=O)C)[C@@H:27]([CH2:38][O:39]C(=O)C)[O:26][C@H:9]1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=O)C>CO>[O:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[C@@H:9]1[O:26][C@H:27]([CH2:38][OH:39])[C@@H:28]([OH:34])[C@H:29]([OH:30])[C@H:8]1[OH:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 120199842-(4-methoxybenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Product 1

HCID 10177526SergliflozinYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (28% methanol solution; 0.12 mL) was added to a solution of 2-(4-methoxybenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.11 g) in methanol (4 mL), and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 2-(4-methoxybenzyl)-phenyl β-D-glucopyranoside (65 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-b5d39dca388146fc9b872bc9f749e36a
Source dataset
uspto-grants-2005_03
Patent number
US06872706B2

Reaction notes

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