Hydrochloric Acid → (R)-3-(2-furylmethyl)-1-(5-hydroxyhexyl)-7-methylxanthine

HRID 1835708ノート

反応式

HRID 1835708 の反応式
C([O:4][C@H:5]([CH3:28])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)[C:11]1=[O:12])(=O)C.Cl.O1CCOCC1>CO>[O:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][N:13]1[C:14]2[N:15]=[CH:16][N:17]([CH3:21])[C:18]=2[C:19](=[O:20])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:28])[C:11]1=[O:12]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 54209961(R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine

生成物 1

HCID 9884609(R)-3-(2-furylmethyl)-1-(5-hydroxyhexyl)-7-methylxanthine収率 80.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirring solution of (R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine (0.42 g, 1.07 mmol) in methanol (20 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4 M, 0.80 ml, 3.21 mmol) and the mixture was refluxed for 5 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was treated with saturated aqueous sodium bicarbonate solution (25 ml) and the mixture was extracted with dichloromethane (3×25 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (2×25 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to provide (R)-3-(2-furylmethyl)-1-(5-hydroxyhexyl)-7-methylxanthine (0.30 g, 80% yield).

後処理

  1. temperaturethe mixture was refluxed for 5 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was treated with saturated aqueous sodium bicarbonate solution (25 ml)
  4. extractionthe mixture was extracted with dichloromethane (3×25 ml)
  5. washThe combined extracts were washed with saturated aqueous sodium chloride solution (2×25 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

出典と根拠

ORDレコード
ord-168ed2dfb5e140d8ae676b9b1c400d04
出典データセット
uspto-grants-2004_08
特許番号
US06774130B2

反応ノート

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