Water → 1-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthine

HRID 361532Notes

Reaction equation

HRID 361532 reaction equation
[CH2:1]([N:13]1[C:22](=[O:23])[C:21]2[N:20]([CH3:24])[CH:19]=[N:18][C:17]=2[N:16]([CH3:25])[C:14]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].C[N+]1([O-])CC[O:30]CC1.[OH2:34].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.O>[OH:34][CH:11]([CH2:12][OH:30])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:13]1[C:22](=[O:23])[C:21]2[N:20]([CH3:24])[CH:19]=[N:18][C:17]=2[N:16]([CH3:25])[C:14]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 23295871HCID 23295871, compound

Product 1

HCID 234356281-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthineYield 84%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 1-(11-Dodecenyl)-3,7-dimethylxanthine (4.70 g, 13.6 mmol), 4-methylmorpholine-N-oxide (4.79 g, 40.7 mmol) and potassium osmate dihydrate (52 mg, 0.14 mmol) in acetone/water 1:2 (75 mL) was stirred for 16 hours. Water (50 mL) and sodium sulfite (5 g) were added and the mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (3×100 mL), dried using magnesium sulfate and evaporated to obtain a pale green solid. Recrystallization from hot ethyl acetate yields 4.32 g (84% yield) 1-(11,12-dihydroxydodecyl)-3,7-dimethylxanthine (inventive compound no. 2517) as a white solid.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (3×100 mL)
  2. customdried
  3. customevaporated
  4. customto obtain a pale green solid
  5. customRecrystallization from hot ethyl acetate

Sources & evidence

ORD record
ord-6b0e51c196f24da7b420dd1ab8044701
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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