Water → (R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthine

HRID 1814926노트

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HRID 1814926 반응식
[C:1]([O:4][C@H:5]([CH3:27])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][O:22][CH2:23][CH3:24])[C:16](Br)=[N:15][C:14]=2[N:13]([CH3:26])[C:11]1=[O:12])(=[O:3])[CH3:2].[I-].[Na+].[C-:30]#[N:31].[K+].O>CS(C)=O>[C:1]([O:4][C@H:5]([CH3:27])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][O:22][CH2:23][CH3:24])[C:16]([C:30]#[N:31])=[N:15][C:14]=2[N:13]([CH3:26])[C:11]1=[O:12])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 5238Sodium IodideHCID 9032Potassium CyanideHCID 54041337(R)-1-(5-acetoxyhexyl)-8-bromo-7-ethoxymethyl-3-methylxanthine

생성물 1

HCID 54159356(R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthine수율 60.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of (R)-1-(5-acetoxyhexyl)-8-bromo-7-ethoxymethyl-3-methylxanthine (1.83 g, 4.11 mmol) and sodium iodide (123 mg, 0.82 mmol) in anhydrous dimethylsulfoxide (40 ml) was added potassium cyanide (294 mg, 4.52 mmol). After stirring at room temperature for 58 hours, the mixture was treated with water (200 ml) and extracted with ethyl acetate (4x 25 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (25 ml) and then dried over magnesium sulfate. After the solvent was evaporated under reduced pressure, the product was purified by flash chromatography on silica get eluting with ethyl acetate-hexane (1:3) to provide (R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthine (970 mg, 60% yield) as a pale yellow oil.

후처리

  1. extractionextracted with ethyl acetate (4x 25 ml)
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution (25 ml)
  3. dry with materialdried over magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe product was purified by flash chromatography on silica
  6. customget
  7. washeluting with ethyl acetate-hexane (1:3)

출처 및 근거

ORD 기록
ord-dfe4f1c54f5141348c4563771ec1c414
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878715B1

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