Reaktionsgleichung
O[CH:2]([CH2:22]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11].[H-].[Na+].N1C(=O)C2N(C)C=NC=2N(C)C1=O.BrCCCCCCC=C>CS(C)=O.O>[CH2:8]([N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:22]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
1-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine (CT1538) was used as an intermediate for the synthesis of CT1514 (example 15). To a suspension of sodium hydride (580 mg, 24.2 mmol) in dimethylsulfoxide (100 ml) was added theobromine (3.96 g, 22.0 mmol). After stirring for 30 min, 8-bromo-1-octene (3.96 g, 22 mmol) was added and the mixture was stirred for 16 hr. The mixture was poured into water (200 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml), dried over sodium sulfate, and the solvent was evaporated under vacuum to give 1-(7-octenyl)-3,7-dimethylxanthine (CT1535) (6.22 g, 97% yield) as an oil which solidified upon standing.
Aufarbeitung
- stirringthe mixture was stirred for 16 hr
- extractionextracted with dichloromethane (3×50 ml)
- washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml)
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-2ce3bf41138e4b8a90a20bc9fcac6066
- Quelldatensatz
- uspto-grants-1997_09
- Patentnummer
- US05670506
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