Trifluoroacetic acid → HCID 54108424, compound
Reaction equation
FC(F)(F)C(O)=O.[C:8]([O:11][C@H:12]([CH3:43])[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:26](=[O:27])[C:25]2[N:24]([CH3:28])[CH:23]=[N:22][C:21]=2[N:20]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35]C(OC(C)(C)C)=O)[C:18]1=[O:19])(=[O:10])[CH3:9]>ClCCl>[C:8]([O:11][C@H:12]([CH3:43])[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:26](=[O:27])[C:25]2[N:24]([CH3:28])[CH:23]=[N:22][C:21]=2[N:20]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])[C:18]1=[O:19])(=[O:10])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (30 ml) was added to a solution of (R)-1-(5-acetoxyhexyl)-3-(N-t-butyloxycarbonyl-6-aminohexyl)-7-methylxanthine (1.37 g) in dichloromethane (30 ml). After stirring at room temperature for 1 hour, the mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (50 ml). The solution was washed with saturated aqueous sodium bicarbonate solution (20 ml), with water (20 ml), with saturated aqueous sodium chloride solution (20 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (R)-1-(5-acetoxyhexyl)-3-(6-aminohexyl)-7-methylxanthine (1.073 g).
Workup
- concentrationthe mixture was concentrated under reduced pressure
- dissolutionThe residue was dissolved in dichloromethane (50 ml)
- washThe solution was washed with saturated aqueous sodium bicarbonate solution (20 ml), with water (20 ml), with saturated aqueous sodium chloride solution (20 ml)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b3e81a4fe96e4614a68708ff4ac996d8
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06774130B2
Reaction notes
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