Hydrogen Bromide → HCID 23287941, compound

HRID 361506Notes

Reaction equation

HRID 361506 reaction equation
[OH:1][CH:2]([CH2:25]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14].[BrH:27].[C:28](=[O:31])(O)[O-].[Na+].Cl[CH2:34]Cl>C(O)(=O)C>[C:28]([O:1][CH:2]([CH2:25][Br:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14])(=[O:31])[CH3:34]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 15885495HCID 15885495, compound

Product 1

HCID 23287941HCID 23287941, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(10,11-Dihydroxyundecanyl)-3,7-dimethylxanthine (3.6 g, 10 mmol) was stirred with hydrogen bromide (6.2 mL, 8.4 g of a 30% solution in acetic acid, 31.1 mmol) for 90 minutes. The mixture was then added to a flask containing 100 mL aqueous sodium bicarbonate solution and 75 mL dichloromethane. After 10 minutes of vigorous stirring the layers were separated and the aqueous portion washed with dichloromethane (3×75 mnL). The organic portions were combined, dried over magnesium sulfate, and evaporated to give 1-(10-acetoxy-11-bromoundecanyl)-3,7-dimethylxanthine (3.6 g). Without further purification, the bromoacetate was taken up in methanol (25 mL) and treated with a solution of sodium methoxide (prepared from 0.28 g, 12.2 mmol sodium, and 25 mL methanol). After 30 minutes, most of the solvent was removed under reduced pressure and the residue extracted with dichloromethane (3×75 mL). The organic portions were combined, dried over magnesium sulfate and concentrated under reduced pressure to obtain an off-white solid which was purified by column chromatography over silica gel using dichloromethane/(3%) methanol eluant to yield 2.0 g (57% yield) 1-(10,11-Oxidoundecanyl)-3,7-dimethylxanthine.

Workup

  1. additionThe mixture was then added to a flask
  2. customwere separated
  3. washthe aqueous portion washed with dichloromethane (3×75 mnL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-25cc4cedf2e24e418eace799319058e6
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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