Sodium Methoxide → 3-(beta-D-glucopyranosyloxy)-5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-1H-pyrazole

HRID 457507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457507
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([O:7][C@@H:8]2[O:25][C@H:24]([CH2:26][O:27]C(=O)C)[C@@H:19]([O:20]C(=O)C)[C@H:14]([O:15]C(=O)C)[C@H:9]2[O:10]C(=O)C)[C:3]=1[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[C:39]2[CH2:41][CH2:40]2)=[CH:34][CH:33]=1.C[O-].[Na+]>CO>[C@@H:8]1([O:7][C:4]2[C:3]([CH2:31][C:32]3[CH:33]=[CH:34][C:35]([CH:38]=[C:39]4[CH2:41][CH2:40]4)=[CH:36][CH:37]=3)=[C:2]([CH3:1])[NH:6][N:5]=2)[O:25][C@H:24]([CH2:26][OH:27])[C@@H:19]([OH:20])[C@H:14]([OH:15])[C@H:9]1[OH:10]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 691337265-Methyl-4-{[4-(cyclopropylidenemethyl)-phenyl]methyl}-3-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyloxy)-1h-pyrazole

Produkt 1

HCID 98440533-(beta-D-glucopyranosyloxy)-5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-1H-pyrazoleAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.010 g) in methanol (2 mL) was added sodium methoxide (28% methanol solution, 0.0020 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 solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give 3-(β-D-glucopyranosyloxy)-5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-1H-pyrazole (0.0070 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationthe residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

Quellen und Nachweise

ORD-Eintrag
ord-be0b15e31e8a4b0eb36eb1aced8fbd23
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189702B2

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