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

HRID 7393ノート

反応式

HRID 7393 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b269f573691d4ca6aca44037f3491647
出典データセット
uspto-grants-2006_08
特許番号
US07087579B2

反応ノート

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