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

HRID 1835699노트

반응식

HRID 1835699 반응식
[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]

참가 물질

7

반응물 4

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

생성물 2

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-962dfb75bbdf4b6c8e57c4259024b174
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774130B2

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