Acetic Acid → 1-(11-Acetoxy-12-bromododecyl)-3,7-dimethylxanthine
Reaction equation
[OH:1][CH:2]([CH2:26]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:24](=[O:25])[C:23]2[N:21]([CH3:22])[CH:20]=[N:19][C:18]=2[N:16]([CH3:17])[C:14]1=[O:15].[BrH:28].O.[Na].[C:31]([OH:34])(=O)[CH3:32]>>[C:31]([O:1][CH:2]([CH2:26][Br:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:24](=[O:25])[C:23]2[N:21]([CH3:22])[CH:20]=[N:19][C:18]=2[N:16]([CH3:17])[C:14]1=[O:15])(=[O:34])[CH3:32]Participants
Procedure
1-(1 1,12-Dihydroxydodecyl)-theobromine, prepared above (2.50 g, 6.58 mmol), was stirred with hydrogen bromide (6.39 ml of a 30% solution in acetic acid, 19.73 mmol) for 2 hours. The mixture was then added over 10 minutes to water (25 ml), ice (30 g) and sodium hydrideCO3 (15 g). The resulting mixture was then stirred for 30 minutes. The mixture was extracted with dichloromethane (3×50 ml), and the organic phases combined and dried with magnesium sulfate. The solvent was evaporated to afford a residue (3.18 g, 99%) of 1-(11-acetoxy-12-bromododecyl)-3,7-dimethylxanthine. Without further purification, this crude product was taken up in methanol (10 ml) and treated with a solution of sodium methoxide (prepared from sodium, 0.160 g, 6.90 mmol, and 20 ml methanol). After 60 minutes, the reaction was added to water (30 ml) and extracted with dichloromethane (3×50 ml). The organic portions were combined, dried and evaporated t produce 2.20 g of a white solid, 1-(1 1,12-oxidododecyl)-3,7-dimethylxanthine (93% yield)
Workup
- extractionThe mixture was extracted with dichloromethane (3×50 ml)
- dry with materialdried with magnesium sulfate
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-6c5af279cbc5467aa679a64259d0d20d
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05770595
Reaction notes
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