Sodium Methoxide → Sergliflozin

HRID 2222074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222074
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

Sodiummethoxide (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-methoxy-benzyl)phenyl β-D-glucopyranoside (65 mg). 1H-NMR (CD3OD) δ ppm: 3.35-3.55 (4H, m), 3.69 (1H, dd, J=5.1, 12.1 Hz), 3.73 (3H, s), 3.80-4.00 (2H, m), 4.03 (1H, d, J=15.1 Hz), 4.91 (1H, d, J=7.4 Hz), 6.75-6.85 (2H, m), 6.85-6.95 (1H, m), 6.95-7.10 (1H, m), 7.10-7.20 (4H, m)

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-6d7cba155373432da75a1874c872b71d
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371730B2

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