Sodium hydride → (S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine

HRID 1835734노트

반응식

HRID 1835734 반응식
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:22]([O:25][C@@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30]Br)(=[O:24])[CH3:23]>CS(C)=O>[C:22]([O:25][C@@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30][N:14]1[C:15](=[O:17])[C:16]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=[N:10][C:11]=2[N:12]([CH3:19])[C:13]1=[O:18])(=[O:24])[CH3:23]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 6856307-Benzyl-3-methylxanthineHCID 54040544(S)-5-acetoxy-1-bromohexane

생성물 1

HCID 53701359(S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine수율 87.8%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a stirring suspension of 7-benzyl-3-methylxanthine (0.512 g, 2 mmol) in dimethyl sulfoxide (10 ml) was added 95% sodium hydride (50.5 mg, 2.0 mmol) in one portion. After stirring for 30 minutes, (S)-5-acetoxy-1-bromohexane (0.490 g, 2.2 mmol) was added neat. After stirring at room temperature for 12 hours, the reaction was quenched by addition of water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 ml), with saturated aqueous sodium chloride solution (50 ml) and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate to give (S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine (0.700 g).

후처리

  1. stirringAfter stirring at room temperature for 12 hours
  2. customthe reaction was quenched by addition of water (50 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 ml), with saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent under reduced pressure
  7. customgave a residue which
  8. customwas purified by flash chromatography on silica gel eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-0e070768584743c98d91ab5a0292096f
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774130B2

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