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

HRID 1814913

反応式

HRID 1814913 の反応式
[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]

参加物

7

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

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 next. (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.

後処理

  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

出典と根拠

ORDレコード
ord-eea38e1cd00243098f2f44ca1f1f7377
出典データセット
uspto-grants-2005_04
特許番号
US06878715B1

関連ノート

読み込み中…