Acetic Acid → HCID 22941884, compound

HRID 361538Notes

Reaction equation

HRID 361538 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 22941883HCID 22941883, compound

Product 1

HCID 22941884HCID 22941884, compound

Procedure

1-(4-(S)-Methyl-7,8-dihydroxy-8-methylnonyl)-3,7-dimethylxanthine (0.37 g, 1.00 mmol) was stirred with hydrogen bromide (1.25 mL of a 30% solution in acetic acid, 3.00 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), and the combined organic phases were dried using magnesium sulfate and the solvent evaporated to yield a residue of 1-(4-(S)-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 were dried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-579661e7ad874952ab9ad7838e4d85b2
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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