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

HRID 7380ノート

反応式

HRID 7380 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 98440533-(beta-D-glucopyranosyloxy)-5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-1H-pyrazole収率 99.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-20c040d52e9041069b9315065b0b9dc3
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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