Water → (R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine

HRID 1835696

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HRID 1835696 반응식
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[NH:5][C:3]1=[O:4].[H-].[Na+].[C:16]([O:19][C@H:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][Br:25])(=[O:18])[CH3:17].O>CS(C)=O>[C:16]([O:19][C@H:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][Br:25])(=[O:18])[CH3:17].[C:16]([O:19][C@H:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][N:5]1[C:6]2[N:7]=[CH:8][N:9]([CH3:13])[C:10]=2[C:11](=[O:12])[N:2]([CH3:1])[C:3]1=[O:4])(=[O:18])[CH3:17]

참가 물질

7

반응물 4

HCID 962WaterHCID 4687ParaxanthineHCID 24758Sodium hydrideHCID 12619445(R)-5-Acetoxy-1-bromohexane

생성물 2

HCID 12619445(R)-5-Acetoxy-1-bromohexaneHCID 54338253(R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine수율 120.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

To a stirring solution of 1,7-dimethylxanthine (0.30 g, 1.67 mmol) in dimethylsulfoxide (20 ml) was added sodium hydride (42 mmg, 1.75 mmol) in one portion. After stirring for 30 minutes, (R)-5-acetoxy-1-bromohexane (0.31 g, 1.75 mmol) was added neat. (R)-5-Acetoxy-1-bromohexane was prepared according to methods described in U.S. patent application Ser. No. 09/002,345, which is incorporated herein by reference. After heating at 80° C. for 18 hours, water (25 ml) was added and the aqueous solution was extracted with dichloromethane (3×20 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (50 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)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine (0.34 g, 64% yield) as a colorless oil.

후처리

  1. extractionthe aqueous solution was extracted with dichloromethane (3×20 ml)
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution (50 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-38e733cee3844851a04ddd5dfa6c63b5
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774130B2

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