Acetic Acid → 1-(16-Acetoxy-17-bromoheptadecyl)-3,7-dimethylxanthine

HRID 1954168Notes

Reaction equation

[OH:1][CH:2]([CH2:31]O)[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][CH2:16][CH2:17][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].[BrH:33].O.C([O-])(O)=O.[Na+].[C:40]([OH:43])(=O)[CH3:41]>>[C:40]([O:1][CH:2]([CH2:31][Br:33])[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][CH2:16][CH2:17][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])(=[O:43])[CH3:41]

Participants

Reactant 5

HCID 176Acetic Acid

HCID 260Hydrogen Bromide

HCID 962Water

HCID 516892Sodium Bicarbonate

HCID 234356301-(16,17-Dihydroxyheptadecyl)-3,7-dimethylxanthine

Product 1

HCID 232958891-(16-Acetoxy-17-bromoheptadecyl)-3,7-dimethylxanthine

Procedure

1-(16,17-Dihydroxyheptadecyl)-3,7-dimethylxanthine (1.10 g, 2.44 mmol) was stirred with HBr (3.50 mL of a 30% solution in acetic acid, 17.1 mmol) for 4 hours. The mixture was then added over 10 minutes to water (50 mL), and NaHCO3 (10 g) and stirred for 30 minutes. The reaction mixture was extracted with dichloromethane (3×30 mL), the combined organic phases were dried using magnesium sulfate and the solvent was evaporated to obtain a residue of 1-(16-acetoxy-17-bromoheptadecyl)-3,7-dimethylxanthine.

Workup

extractionThe reaction mixture was extracted with dichloromethane (3×30 mL)
customthe combined organic phases were dried
customthe solvent was evaporated

Sources & evidence

ORD record: ord-7e28bfdb9d8a4b0ba98785b4b96c353c
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121270

Reaction notes

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