Sodium Methoxide → Sergliflozin

HRID 1825320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825320
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-d71823fd08224bdb8dbbbc165ad09238
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045665B2

Notizen zur Reaktion

Wird geladen…