Water → 1-(12,13-Dihydroxytridecyl)-3,7-dimethylxanthine

HRID 1954160Notes

Reaction equation

HRID 1954160 reaction equation
[CH2:1]([N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[N:17]([CH3:26])[C:15]1=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13].C[N+]1([O-])CC[O:31]CC1.[OH2:35].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.O>[OH:35][CH:12]([CH2:13][OH:31])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[N:17]([CH3:26])[C:15]1=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 154868371-(12-Tridecenyl)-3,7-dimethylxanthine

Product 1

HCID 154868381-(12,13-Dihydroxytridecyl)-3,7-dimethylxanthineYield 82%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 1-(12-Tridecenyl)-3,7-dimethylxanthine (1.39 g, 3.86 mmol), 4-methylmorpholine-N-oxide (1.36 g, 11.6 mmol) and potassium osmate dihydrate (14 mg, 0.040 mmol) in acetone/water 1:2 (25 mL) was stirred for 16 hours. Water (25 mL) and sodium sulfite (2 g) were added and the reaction mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (3×50 mL), dried using magnesium sulfate and the solvent evaporated to yield 1.25 g (82%) of 1-(12,13-dihydroxytridecyl)-3,7-dimethylxanthine (inventive compound no. 2556) as a white solid.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (3×50 mL)
  2. customdried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-6d5a18f426d741ff921e8e5a0b3b3c5f
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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