Acetone → HCID 15885495, compound

HRID 361505Notes

Reaction equation

HRID 361505 reaction equation
[CH2:1]([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])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]CC=C.C[N+]1([O-])CC[O:29]CC1.S([O-])([O-])=O.[Na+].[Na+].[CH3:39][C:40]([CH3:42])=[O:41]>O>[OH:41][CH:40]([CH2:42][OH:29])[CH2:39][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][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]

Participants

6

Reactant 4

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 158854941-(10-Undecenyl)-3,7-dimethylxanthine

Product 1

HCID 15885495HCID 15885495, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of l-(10-undecenyl)-3,7-dimethylxanthine (4.3 g, 13 mmol), 4-methylmorpholine-N-oxide (1.942 g, 16.6 mmol) and potassium osmate dihydrate (9.5 mg; 0.026 mmol) in acetone (45 mL) and water (10 mL) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (12 rnl) was added and stirred for 30 minutes. The reaction mixture was extracted with 25% ethanol/dichloromethane (4×100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by flash chromatography over silica gel using methanol (5%)/dichloromethane eluant to yield 3.6 g (76% yield) 1-(10,11-dihydroxyundecanyl)-3,7-dimethylxanthine (inventive compound no. 1592).

Workup

  1. extractionThe reaction mixture was extracted with 25% ethanol/dichloromethane (4×100 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-e92ffc2fb52d4fc0a7f7cd64f3dd2490
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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