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

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Reaction Steps

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 hydrochloric 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 awhite solid.

Provenance & Evidence