Cesium carbonate → 4-[(4-ethylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-1H-pyrazole

HRID 7393

Reaktionsgleichung

Reaktionsgleichung von HRID 7393
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11]([O:16][C@@H:17]3[O:34][C@H:33]([CH2:35][O:36]C(=O)C)[C@@H:28]([O:29]C(=O)C)[C@H:23]([O:24]C(=O)C)[C@H:18]3[O:19]C(=O)C)=[N:12][NH:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:46]([O:53]CCCBr)[C:47]1C=CC=C[CH:48]=1.[OH-].[Na+]>C(#N)C.O.CO>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11]([O:16][C@@H:17]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:28]([OH:29])[C@H:23]([OH:24])[C@H:18]3[OH:19])=[N:12][N:13]([CH2:48][CH2:47][CH2:46][OH:53])[C:14]=2[CH3:15])=[CH:5][CH:4]=1)[CH3:2]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 2776064Benzyl 3-Bromopropyl EtherHCID 673355784-[(4-Ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Produkt 1

HCID 690132554-[(4-ethylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 4-[(4-ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.030 g) and cesium carbonate (0.091 g) in acetonitrile (0.4 mL) was added benzyl(3-bromopropyl)ether (0.039 mL), and the mixture was stirred at 80° C. for 30 minutes. To the reaction mixture were added methanol (0.4 mL) and 2 mol/L aqueous sodium hydroxide solution (0.55 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol). To the resulting eluent was added a catalytic amount of 10% palladium-carbon powder, and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 days. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by liquid chromatography on ODS (eluent: methanol/water=40/60) to give 4-[(4-ethylphenyl)methyl]-3-(β-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-1H-pyrazole (0.0080 g).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. distillationthe mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)
  3. additionTo the resulting eluent was added a catalytic amount of 10% palladium-carbon powder
  4. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere for 3 days
  5. customInsoluble materials were removed by filtration
  6. customthe solvent of the filtrate was removed under reduced pressure
  7. customThe residue was purified by liquid chromatography on ODS (eluent: methanol/water=40/60)

Quellen und Nachweise

ORD-Eintrag
ord-b269f573691d4ca6aca44037f3491647
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087579B2

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