Water → 1-(9,10-Dihydroxyoctadecyl)-3,7-dimethylxanthine

HRID 1870854

反応式

HRID 1870854 の反応式
[CH2:1]([N:19]1[C:28](=[O:29])[C:27]2[N:26]([CH3:30])[CH:25]=[N:24][C:23]=2[N:22]([CH3:31])[C:20]1=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C[N+]1([O-])CC[O:36]CC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:46]>CC(C)=O>[OH:46][CH:9]([CH:10]([OH:36])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:19]1[C:28](=[O:29])[C:27]2[N:26]([CH3:30])[CH:25]=[N:24][C:23]=2[N:22]([CH3:31])[C:20]1=[O:21]

参加物

6

反応物 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 537845551-(9-Octadecenyl)-3,7-dimethylxanthine

生成物 1

HCID 234356351-(9,10-Dihydroxyoctadecyl)-3,7-dimethylxanthine収率 40.4%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 1-(9-octadecenyl)-3,7-dimethylxanthine (0.15 g, 0.35 mmol), 4-methylmorpholine-N-oxide (49 mg, 0.42 mmol, 1.2 equivalents.) and potassium osmate dihydrate (1 mg) in acetone (4 ml) and water (1 ml) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (2 ml) was added and stirred for 30 minutes. The reaction mixture was extracted with four 10 ml aliquots of 25% ethanol/dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, the solvent evaporated under reduced pressure and a residue purified by flash chromatography over silica gel using a methanol(5%)/dichloromethane eluant, yielding 0.65 g of 1-(9,10-dihydroxyoctadecyl)-3,7-dimethylxanthine (40.4% yield).

後処理

  1. extractionThe reaction mixture was extracted with four 10 ml aliquots of 25% ethanol/dichloromethane
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. customthe solvent evaporated under reduced pressure
  4. customa residue purified by flash chromatography over silica gel using a methanol(5%)/dichloromethane eluant

出典と根拠

ORDレコード
ord-eff17d1969c94dc2b1f9579476832299
出典データセット
uspto-grants-2000_08
特許番号
US06100271

関連ノート

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