Water → 1-(16,17-Dihydroxyheptadecyl)-3,7-dimethylxanthine
Reaction equation
[CH2:1]([N:18]1[C:27](=[O:28])[C:26]2[N:25]([CH3:29])[CH:24]=[N:23][C:22]=2[N:21]([CH3:30])[C:19]1=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17].C[N+]1([O-])CC[O:35]CC1.[OH2:39].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.O.O1CCCC1>[OH:39][CH:16]([CH2:17][OH:35])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:18]1[C:27](=[O:28])[C:26]2[N:25]([CH3:29])[CH:24]=[N:23][C:22]=2[N:21]([CH3:30])[C:19]1=[O:20]Participants
6
Procedure
A solution of 1-(16-Heptadecenyl)-3,7-dimethylxanthine (1.50 g, 3.60 mmol), 4-methylmorpholine-N-oxide (1.83 mL, 60% wt in water, 10.6 mmol) and potassium osmate dihydrate (16 mg, 0.04 mmol) in acetone/water/ tetrahydrofuran (10:7:5, 110 mL) was stirred for 60 hours. Water (100 mL) and sodium sulfite (1 g) were added and the reaction mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (2×100 mL) and the organic phase dried using magnesium sulfate and the solvent evaporated to afford a cream solid. Recrystallization from hot ethyl acetate yields 1.31 g (81% yield) of 1-(16,17-dihydroxyheptadecyl)-3,7-dimethylxanthine (inventive compound no. 3514).
Workup
- extractionThe reaction mixture was extracted with dichloromethane (2×100 mL)
- customthe organic phase dried
- customthe solvent evaporated
- customto afford a cream solid
- customRecrystallization from hot ethyl acetate
Sources & evidence
- ORD record
- ord-2df91c9668b14d34989866dcbb8964ae
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866576
Reaction notes
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