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

HRID 1835708노트

반응식

HRID 1835708 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-168ed2dfb5e140d8ae676b9b1c400d04
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774130B2

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