Acetic Acid → 1-(12-Acetoxy-13-bromotridecyl)-3,7-dimethylxanthine
Reaction equation
[OH:1][CH:2]([CH2:27]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[N:17]([CH3:26])[C:15]1=[O:16].[BrH:29].O.C(=O)(O)[O-].[Na+].[C:36]([OH:39])(=O)[CH3:37]>>[C:36]([O:1][CH:2]([CH2:27][Br:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[N:17]([CH3:26])[C:15]1=[O:16])(=[O:39])[CH3:37]Participants
Procedure
1-(12,13-Dihydroxy-tridecyl)-3,7-dimethylxanthine (1.15 g, 2.92 mmol) was stirred with hydrogen bromide (2.84 mL of a 30% solution in acetic acid, 8.76 mmol) for 2 hours. The mixture was then added over 10 minutes to water (20 mL), ice (15 g) and sodium bicarbonate (5 g) and stirred for 30 minutes. The reaction mixture was extracted with dichloromethane (2×50 mL), and the combined organic phases were dried using magnesium sulfate and the solvent evaporated to obtain a residue of 1-(12-acetoxy-13-bromotridecyl)-3,7-dimethylxanthine. Without further purification, this crude residue was taken up in methanol (5 mL) and treated with a solution of sodium methoxide (prepared from sodium, 0.069 g, 3.00 mmol, and 5 mL methanol). After 40 minutes, the reaction mitxure was added to water (15 mL) and extracted with dichloromethane (3×30 mL). The organic portions were combined, dried and the solvent evaporated to yield 1.00 g (91% yield) 1-(12,13-Oxidotridecyl)-3,7-dimethylxanthine (inventive compound no. 2562) as a white solid.
Workup
- extractionThe reaction mixture was extracted with dichloromethane (2×50 mL)
- customthe combined organic phases were dried
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-6060f034632a4a4fafc6e29fc47858b3
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866576
Reaction notes
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