Water → (R)-1-(5-acetoxyhexyl)-9-pivaloyloxymethyl-3,7-dimethyluric acid

HRID 1814915Notes

Reaction equation

HRID 1814915 reaction equation
[C:1]([O:7][CH2:8][N:9]1[C:17](=[O:18])[N:16]([CH3:19])[C:15]2[C:14](=[O:20])[NH:13][C:12](=[O:21])[N:11]([CH3:22])[C:10]1=2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Na+].[C:25]([O:28][C@H:29]([CH3:35])[CH2:30][CH2:31][CH2:32][CH2:33][I:34])(=[O:27])[CH3:26].O>CS(C)=O>[C:25]([O:28][C@H:29]([CH3:35])[CH2:30][CH2:31][CH2:32][CH2:33][I:34])(=[O:27])[CH3:26].[C:25]([O:28][C@H:29]([CH3:35])[CH2:30][CH2:31][CH2:32][CH2:33][N:13]1[C:14](=[O:20])[C:15]2[N:16]([CH3:19])[C:17](=[O:18])[N:9]([CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[C:10]=2[N:11]([CH3:22])[C:12]1=[O:21])(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 224990389-Pivaloyloxymethyl-3,7-dimethyluric acidHCID 54009360(R)-5-acetoxy-1-iodohexane

Product 2

HCID 53725271(R)-1-(5-acetoxyhexyl)-9-pivaloyloxymethyl-3,7-dimethyluric acidYield 94%HCID 54009360(R)-5-acetoxy-1-iodohexane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirring solution of 9-pivaloyloxymethyl-3,7-dimethyluric acid (0.14 g, 0.45 mmol) in dimethylsulfoxide (10 ml) was added sodium hydride (12 mg, 0.47 mmol) in one portion. The solution was stirred for 15 minutes. (R)-5-Acetoxy-1-iodohexane (0.13 g, 0.47 mmol) in dimethylsulfoxide (1 ml) was added. The solution of (R)-5-acetoxy-1-iodohexane was prepared according to methods described in U.S. patent application Ser. No. 09/002,345, which is incorporated herein by reference. After stirring at room temperature for 24 hours, water (25 ml) was added and the aqueous solution was extracted with ethyl acetate (3×15 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (15 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica eluting with ethyl acetate to give (R)-1-(5-acetoxyhexyl)-9-pivaloyloxymethyl-3,7-dimethyluric acid (0.10 g, 50% yield) as a white solid.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. extractionthe aqueous solution was extracted with ethyl acetate (3×15 ml)
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution (15 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-8f8b512d1b1343efb7a1e1e4a72b6d28
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

Loading…