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Sodium hydride → (R)-1-(5-acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine

HRID 1421232
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1421232
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[C:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:23]([O:26][C@H:27]([CH3:33])[CH2:28][CH2:29][CH2:30][CH2:31]Cl)(=[O:25])[CH3:24]>CS(C)=O>[C:23]([O:26][C@H:27]([CH3:33])[CH2:28][CH2:29][CH2:30][CH2:31][N:14]1[C:15](=[O:17])[C:16]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:9]([CH3:20])=[N:10][C:11]=2[N:12]([CH3:19])[C:13]1=[O:18])(=[O:25])[CH3:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 110194345-(R)-Acetoxy-1-chlorohexaneHCID 147126087-Benzyl-3,8-dimethylxanthine

Produkt 1

HCID 54438002(R)-1-(5-acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

7-Benzyl-3,8-dimethylxanthine (500 mg, 1.85 mmol) was added to a suspension of sodium hydride (50.5 mg) in anhydrous DMSO (20 ml) and stirred for 30 min. (R)-5-acetoxy-1-chlorohexane (357 mg) (prepared according to Kline et al. U.S. Pat. No. 5,629,423 (1997)) was added and the mixture was heated at 70-80° C. for 12 h. After cooling to room temperature, the reaction was quenched by the addition of water (50 ml) and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with water (2×50 ml), with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. The product was purified by flash chromatography (silica gel) eluting with ethyl acetate. Yield=638 mg.

Aufarbeitung

  1. customprepared
  2. addition5,629,423 (1997)) was added
  3. temperatureAfter cooling to room temperature
  4. customthe reaction was quenched by the addition of water (50 ml)
  5. extractionextracted with ethyl acetate (3×75 ml)
  6. washThe combined extracts were washed with water (2×50 ml), with saturated aqueous sodium chloride solution (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (silica gel)
  10. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4f19d0c86fdb439cb02e2a63be4433b0
Quelldatensatz
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06075029

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