Water → (R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthine

HRID 1835712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835712
[C:1]([O:4][C@H:5]([CH3:27])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][O:22][CH2:23][CH3:24])[C:16](Br)=[N:15][C:14]=2[N:13]([CH3:26])[C:11]1=[O:12])(=[O:3])[CH3:2].[I-].[Na+].[C-:30]#[N:31].[K+].O>CS(C)=O>[C:1]([O:4][C@H:5]([CH3:27])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][O:22][CH2:23][CH3:24])[C:16]([C:30]#[N:31])=[N:15][C:14]=2[N:13]([CH3:26])[C:11]1=[O:12])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5238Sodium IodideHCID 9032Potassium CyanideHCID 54041337(R)-1-(5-acetoxyhexyl)-8-bromo-7-ethoxymethyl-3-methylxanthine

Produkt 1

HCID 54159356(R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthineAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-(5-acetoxyhexyl)-8-bromo-7-ethoxymethyl-3-methylxanthine (1.83 g, 4.11 mmol) and sodium iodide (123 mg, 0.82 mmol) in anhydrous dimethylsulfoxide (40 ml) was added potassium cyanide (294 mg, 4.52 mmol). After stirring at room temperature for 58 hours, the mixture was treated with water (200 ml) and extracted with ethyl acetate (4×25 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (25 ml) and then dried over magnesium sulfate. After the solvent was evaporated under reduced pressure, the product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide (R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthine (970 mg, 60% yield) as a pale yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate (4×25 ml)
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution (25 ml)
  3. dry with materialdried over magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-70d736b634734504a5180466562e165e
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774130B2

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