Water → (R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine

HRID 1835696

Reaktionsgleichung

Reaktionsgleichung von HRID 1835696
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[NH:5][C:3]1=[O:4].[H-].[Na+].[C:16]([O:19][C@H:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][Br:25])(=[O:18])[CH3:17].O>CS(C)=O>[C:16]([O:19][C@H:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][Br:25])(=[O:18])[CH3:17].[C:16]([O:19][C@H:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][N:5]1[C:6]2[N:7]=[CH:8][N:9]([CH3:13])[C:10]=2[C:11](=[O:12])[N:2]([CH3:1])[C:3]1=[O:4])(=[O:18])[CH3:17]

Komponenten

7

Edukt 4

HCID 962WaterHCID 4687ParaxanthineHCID 24758Sodium hydrideHCID 12619445(R)-5-Acetoxy-1-bromohexane

Produkt 2

HCID 12619445(R)-5-Acetoxy-1-bromohexaneHCID 54338253(R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthineAusbeute 120,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirring solution of 1,7-dimethylxanthine (0.30 g, 1.67 mmol) in dimethylsulfoxide (20 ml) was added sodium hydride (42 mmg, 1.75 mmol) in one portion. After stirring for 30 minutes, (R)-5-acetoxy-1-bromohexane (0.31 g, 1.75 mmol) was added neat. (R)-5-Acetoxy-1-bromohexane was prepared according to methods described in U.S. patent application Ser. No. 09/002,345, which is incorporated herein by reference. After heating at 80° C. for 18 hours, water (25 ml) was added and the aqueous solution was extracted with dichloromethane (3×20 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica eluting with ethyl acetate to give (R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine (0.34 g, 64% yield) as a colorless oil.

Aufarbeitung

  1. extractionthe aqueous solution was extracted with dichloromethane (3×20 ml)
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution (50 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-38e733cee3844851a04ddd5dfa6c63b5
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774130B2

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