Sodium Methoxide → HCID 69014017, Verbindung

HRID 457509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457509
[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]

Komponenten

4

Edukt 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

Produkt 1

HCID 69014017HCID 69014017, VerbindungAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ccc3d49f04de4335ab65f477829f0108
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189702B2

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