Acetone → 3-(8,9-Dihydroxynonyl)-1-methylthymine
Reaction equation
[CH2:1]([N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]CC=C.C[N+]1([O-])CC[O:24]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:36][C:37]([CH3:39])=[O:38]>O>[OH:38][CH:37]([CH2:39][OH:24])[CH2:36][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-(8-nonenyl)-1-methylthymine (CT1917) (2.63 g, 9.9 mmol), 4-methylmorpholine-N oxide (1.39 g, 12 mmol), and potassium osmate (IV) dihydrate (7 mg, 2×10-5 mmol) in acetone (20 ml) and water (10 ml) was stirred for 18 hr. After addition of saturated aqueous sodium hydrosulfite solution (10 ml), and stirring for 15 min, the mixture was extracted with 20% methanol-dichloromethane (2×50 ml). The combined organic layers were washed with water (15 ml), with saturated aqueous sodium chloride solution (15 ml), and dried over sodium sulfate. The solvent was evaporated under vacuum to give a solid which was recrystallized (ethanol) to give 3-(8,9-dihydroxynonyl)-1-methylthymine (CT1918) (2.68 g, 91% yield).
Workup
- extractionthe mixture was extracted with 20% methanol-dichloromethane (2×50 ml)
- washThe combined organic layers were washed with water (15 ml), with saturated aqueous sodium chloride solution (15 ml)
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under vacuum
- customto give a solid which
- customwas recrystallized (ethanol)
Sources & evidence
- ORD record
- ord-e2a4385b14a74621b8e00d405101058a
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05670506
Reaction notes
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