Acetic Acid → 1-(7-Acetoxy-8-bromooctyl)-3,7-dimethylxanthine

HRID 1954103Notes

Reaction equation

HRID 1954103 reaction equation
[OH:1][CH:2]([CH2:22]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11].[BrH:24].[C:25]([OH:28])(=O)[CH3:26].C(=O)(O)[O-].[Na+]>ClCCl>[C:25]([O:1][CH:2]([CH2:22][Br:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11])(=[O:28])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 97973341-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine

Product 1

HCID 98239441-(7-Acetoxy-8-bromooctyl)-3,7-dimethylxanthineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(7,8-dihydroxyoctyl)-3,7-dimethylxanthine, prepared as described above, (2.11 g, 6 mmol) was stirred with a 30% solution of hydrogen bromide in acetic acid (3.58 mL, 18 mmol) for 90 minutes. The mixture was then added to a flask containing aqueous sodium bicarbonate solution (4 g in 50 mL) and dichloromethane (30 mL). After 10 minutes of vigorous stirring the layers were separated and the aqueous portion was washed with dichloromethane (2×50 mL). The combined organic portions were dried over sodium sulfate and the solvent was evaporated under vacuum, yielding 2.51 g (94%) 1-(7-acetoxy-8-bromooctyl)-3,7-dimethylxanthine (inventive compound no. 1514) as a yellow oil.

Workup

  1. customprepared
  2. additionThe mixture was then added to a flask
  3. customwere separated
  4. washthe aqueous portion was washed with dichloromethane (2×50 mL)
  5. dry with materialThe combined organic portions were dried over sodium sulfate
  6. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-7adcd84ed739485c89c1861c3ff0026d
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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