Hydrochloric Acid → (R)-1-(5-hydroxyhexyl)-3,7-dimethyluric acid

HRID 1814916Notes

Reaction equation

HRID 1814916 reaction equation
C([O:4][C@H:5]([CH3:32])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:20](=[O:21])[C:19]2[N:18]([CH3:22])[C:16](=[O:17])[N:15](COC(=O)C(C)(C)C)[C:14]=2[N:13]([CH3:31])[C:11]1=[O:12])(=O)C.C[O-].[Na+].Cl>CO>[OH:4][C@H:5]([CH3:32])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:20](=[O:21])[C:19]2[N:18]([CH3:22])[C:16](=[O:17])[NH:15][C:14]=2[N:13]([CH3:31])[C:11]1=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 53725271(R)-1-(5-acetoxyhexyl)-9-pivaloyloxymethyl-3,7-dimethyluric acid

Product 1

HCID 11601789(R)-1-(5-hydroxyhexyl)-3,7-dimethyluric acidYield 30.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of (R)-1-(5-acetoxyhexyl)-9-pivaloyloxymethyl-3,7-dimethyluric acid (0.10 g, 0.22 mmol) in methanol (5 ml) was added solid sodium methoxide (48 mg, 0.88 mmol) in one portion. After stirring at room temperature for 4 days, the mixture was treated with 5% aqueous hydrochloride acid solution (0.25 ml) and concentrated under a stream of nitrogen and mild heating. The residue was purified by preparative thin layer chromatography (250 micron silica gel plate) eluting with 7% methanol-dichloromethane to provide (R)-1(5-hydroxyhexyl)-3,7-dimethyluric acid (20 mg, 30% yield) as a white solid.

Workup

  1. concentrationconcentrated under a stream of nitrogen and mild heating
  2. customThe residue was purified by preparative thin layer chromatography (250 micron silica gel plate)
  3. washeluting with 7% methanol-dichloromethane

Sources & evidence

ORD record
ord-63602411cd724d439c7bfe2293c5ff9b
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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