Potassium Cyanide → (R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthine

HRID 1835716노트

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HRID 1835716 반응식
[C:1]([O:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16](Br)=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12])(=[O:3])[CH3:2].[C-:31]#[N:32].[K+]>CS(C)=O>[C:1]([O:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([C:31]#[N:32])=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 9032Potassium CyanideHCID 54190334(R)-1-(5-Acetoxyhexyl)-7-benzyl-8-bromo-3-methylxanthine

생성물 1

HCID 53812008(R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthine수율 90%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
75 °C

실험 절차

To a solution of (R)-1-(5-acetoxyhexyl)-7-benzyl-8-bromo-3-methylxanthine (9.55 g, 20.0 mmol) in anhydrous dimethylsulfoxide was added potassium cyanide (1.43 g, 22.0 mmol). After stirring at 70-80° C. for 4.5 hours, the mixture was cooled to room temperature, quenched with water (500 ml) and extracted with ethyl acetate (4×150 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (45 ml), dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to provide (R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthine (7.60 g, 90% yield) as a beige powder.

후처리

  1. temperaturethe mixture was cooled to room temperature
  2. customquenched with water (500 ml)
  3. extractionextracted with ethyl acetate (4×150 ml)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (45 ml)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1)

출처 및 근거

ORD 기록
ord-08972332c7154570be0419aa22ed38fb
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774130B2

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