Acetic Acid → 1-(4-(R)-methyl-7-acetoxy-8-bromo-8-methylnonyl)-3,7-dimethylxanthine

HRID 1954155Notes

Reaction equation

HRID 1954155 reaction equation
[CH3:1][C@@H:2]([CH2:19][CH2:20][CH:21]([OH:26])[C:22](O)([CH3:24])[CH3:23])[CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8].[BrH:27].O.C(=O)(O)[O-].[Na+].[C:34]([OH:37])(=O)[CH3:35]>>[CH3:1][C@@H:2]([CH2:19][CH2:20][CH:21]([O:26][C:34](=[O:37])[CH3:35])[C:22]([Br:27])([CH3:24])[CH3:23])[CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 516892Sodium BicarbonateHCID 22941881HCID 22941881, compound

Product 1

HCID 229418821-(4-(R)-methyl-7-acetoxy-8-bromo-8-methylnonyl)-3,7-dimethylxanthine

Procedure

1-(4-(R)-Methyl-7,8-dihydroxy-8-methylnonyl)-3,7-dimethylxanthine (0.29 g, 0.80 mmol) was stirred with hydrogen bromide (1.00 mL of a 30% solution in acetic acid, 2.40 mmol) for 4 hours. The mixture was then added over 10 minutes to water (10 mL), ice (5 g) and sodium bicarbonate (2 g) and stirred for 30 minutes. The reaction mixture was extracted with dichloromethane (2×15 mL), the combined organic phases dried using magnesium sulfate and the solvent evaporated to obtain a residue of 1-(4-(R)-methyl-7-acetoxy-8-bromo-8-methylnonyl)-3,7-dimethylxanthine.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (2×15 mL)
  2. customthe combined organic phases dried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-32b3a886f742494eb47cff3235a3c4d9
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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