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

HRID 1835699Notes

Reaction equation

HRID 1835699 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-962dfb75bbdf4b6c8e57c4259024b174
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

Loading…