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

HRID 2393354

Reaktionsgleichung

Reaktionsgleichung von HRID 2393354
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 234356351-(9,10-Dihydroxyoctadecyl)-3,7-dimethylxanthineAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-88a424f2199b415cb9e4229c04fd3ff6
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807862

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