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

HRID 1835708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835708
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 9884609(R)-3-(2-furylmethyl)-1-(5-hydroxyhexyl)-7-methylxanthineAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-168ed2dfb5e140d8ae676b9b1c400d04
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774130B2

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