Water → 1-(4-(S)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthine

HRID 361537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361537
[NH:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3].[Na].CS([CH2:19][CH2:20][CH2:21][C@@H:22]([CH3:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])(=O)=O.O>CS(C)=O>[CH3:29][C@@H:22]([CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH2:21][CH2:20][CH2:19][N:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 228614901-methanesulfonyl-4-(S)-methyl-8-methylnon-7-eneHCID 66980828Theobromine sodium

Produkt 1

HCID 228614871-(4-(S)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of sodium theobromine (4.05 g, 20.0 mmol) in dimethylsulfoxide (50 mL) was added 1-methanesulfonyl-4-(S)-methyl-8-methylnon-7-ene and the reaction stirred for 16 hours at 60° C. The mixture was then poured into water (100 mL) and extracted with ethyl acetate (100 mL, 2×50 mL). The organic portions were combined, dried using magnesium sulfate, and evaporated to give a residue which was purified by column chromatography (ethyl acetate/hexane) to yield 1.83 g (30% yield) 1-(4-(S)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthine (inventive compound no. 2536S) as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (100 mL, 2×50 mL)
  2. customdried
  3. customevaporated
  4. customto give a residue which
  5. customwas purified by column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1f17bbdc6a9142a5b92b19f1b010fec2
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

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