Sodium Methoxide → Sergliflozin

HRID 2375142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375142
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 10177526SergliflozinAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3e355f4c65a5401296839c95d1a4ba49
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465712B2

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