Cesium carbonate → 1-(2-benzyloxyethyl)-4-[(4-ethylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-methyl-1H-pyrazole

HRID 7385

Reaktionsgleichung

Reaktionsgleichung von HRID 7385
[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][CH2:54][CH2:55]Br)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[OH-].[Na+]>C(#N)C.O.CO>[CH2:46]([O:53][CH2:54][CH2:55][N:13]1[C:14]([CH3:15])=[C:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=2)[C:11]([O:16][C@@H:17]2[O:34][C@H:33]([CH2:35][OH:36])[C@@H:28]([OH:29])[C@H:23]([OH:24])[C@H:18]2[OH:19])=[N:12]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 673355784-[(4-Ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Produkt 1

HCID 691337331-(2-benzyloxyethyl)-4-[(4-ethylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-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(2-bromoethyl)ether (0.035 mL), and the mixture was stirred at 80° C. for 30 minutes. After cooling to room temperature, the reaction mixture was further stirred overnight. 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 for 1 hour. Water was added to the reaction mixture, and the mixture was purified by CBA solid phase extraction (washing solvent: distilled water, eluent: methanol), and successively by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give to give 1-(2-benzyloxyethyl)-4-[(4-ethylphenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole (0.012 g).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. waitthe reaction mixture was further stirred overnight
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. distillationthe mixture was purified by CBA solid phase extraction (washing solvent: distilled water, eluent: methanol)
  5. customsuccessively by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give

Quellen und Nachweise

ORD-Eintrag
ord-109fe8804b6a4af0845004d8cdb6b4e7
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087579B2

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