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Sodium hydride → (R)-1-(5-acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine

HRID 1421232
ノート
印刷プレビュー

反応式

HRID 1421232 の反応式
[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]=[C:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:23]([O:26][C@H:27]([CH3:33])[CH2:28][CH2:29][CH2:30][CH2:31]Cl)(=[O:25])[CH3:24]>CS(C)=O>[C:23]([O:26][C@H:27]([CH3:33])[CH2:28][CH2:29][CH2:30][CH2:31][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)[C:9]([CH3:20])=[N:10][C:11]=2[N:12]([CH3:19])[C:13]1=[O:18])(=[O:25])[CH3:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 110194345-(R)-Acetoxy-1-chlorohexaneHCID 147126087-Benzyl-3,8-dimethylxanthine

生成物 1

HCID 54438002(R)-1-(5-acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
75 °C

実験手順

7-Benzyl-3,8-dimethylxanthine (500 mg, 1.85 mmol) was added to a suspension of sodium hydride (50.5 mg) in anhydrous DMSO (20 ml) and stirred for 30 min. (R)-5-acetoxy-1-chlorohexane (357 mg) (prepared according to Kline et al. U.S. Pat. No. 5,629,423 (1997)) was added and the mixture was heated at 70-80° C. for 12 h. After cooling to room temperature, the reaction was quenched by the addition of water (50 ml) and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with water (2×50 ml), with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. The product was purified by flash chromatography (silica gel) eluting with ethyl acetate. Yield=638 mg.

後処理

  1. customprepared
  2. addition5,629,423 (1997)) was added
  3. temperatureAfter cooling to room temperature
  4. customthe reaction was quenched by the addition of water (50 ml)
  5. extractionextracted with ethyl acetate (3×75 ml)
  6. washThe combined extracts were washed with water (2×50 ml), with saturated aqueous sodium chloride solution (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (silica gel)
  10. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-4f19d0c86fdb439cb02e2a63be4433b0
出典データセット
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06075029

反応ノート

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