Sodium hydride → (S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine

HRID 1835734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835734
[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]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:22]([O:25][C@@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30]Br)(=[O:24])[CH3:23]>CS(C)=O>[C:22]([O:25][C@@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30][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)[CH:9]=[N:10][C:11]=2[N:12]([CH3:19])[C:13]1=[O:18])(=[O:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 6856307-Benzyl-3-methylxanthineHCID 54040544(S)-5-acetoxy-1-bromohexane

Produkt 1

HCID 53701359(S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthineAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirring suspension of 7-benzyl-3-methylxanthine (0.512 g, 2 mmol) in dimethyl sulfoxide (10 ml) was added 95% sodium hydride (50.5 mg, 2.0 mmol) in one portion. After stirring for 30 minutes, (S)-5-acetoxy-1-bromohexane (0.490 g, 2.2 mmol) was added neat. After stirring at room temperature for 12 hours, the reaction was quenched by addition of water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 ml), with saturated aqueous sodium chloride solution (50 ml) and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate to give (S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine (0.700 g).

Aufarbeitung

  1. stirringAfter stirring at room temperature for 12 hours
  2. customthe reaction was quenched by addition of water (50 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 ml), with saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent under reduced pressure
  7. customgave a residue which
  8. customwas purified by flash chromatography on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0e070768584743c98d91ab5a0292096f
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774130B2

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