Water → HCID 23435624, compound

HRID 964550Notes

Reaction equation

HRID 964550 reaction equation
[CH2:1]([N:15]1[C:24](=[O:25])[C:23]2[N:22]([CH3:26])[CH:21]=[N:20][C:19]=2[N:18]([CH3:27])[C:16]1=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14].C[N+]1([O-])CC[O:32]CC1.[OH2:36].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.O>[OH:36][CH:13]([CH2:14][OH:32])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:15]1[C:24](=[O:25])[C:23]2[N:22]([CH3:26])[CH:21]=[N:20][C:19]=2[N:18]([CH3:27])[C:16]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 23295971HCID 23295971, compound

Product 1

HCID 23435624HCID 23435624, compoundYield 96%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 1-(13-tetradecenyl)-3,7-dimethylxanthine (2.00 g, 5.35 mmol), 4-methylmorpholine-N-oxide (2.72 ml, 60% wt. in water, 15.8 mmol) and potassium osmate dihydrate (21 mg, 0.05 mmol) in acetone/water, in a ratio of 3:1 (80 mL), was stirred for 16 hours. Water (100 ml) and sodium sulfite (1 g) were added and stirred for 1 hour. The reaction mixture was extracted with dichloromethane (3×100 ml) and the organic phase dried over magnesium sulfate. The solvent was evaporated to obtain 2.1 g of 1-(13,14-dihydroxytetradecyl)-3,7-dimethylxanthine as a white solid (96% yield).

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (3×100 ml)
  2. dry with materialthe organic phase dried over magnesium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-74bd713ee97e48ac8b59ef3e9117c5bc
Source dataset
uspto-grants-1998_06
Patent number
US05770595

Reaction notes

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