(R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine → (R)-(-)-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979465

Reaktionsgleichung

Reaktionsgleichung von HRID 1979465
Cl.O1CCOCC1.[O:8]=[C:9]1[NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[N:12]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:11][C@H:10]1[NH:26]C(OC(C)(C)C)=O>C(O)C>[O:8]=[C:9]1[NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[N:12]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:11][C@H:10]1[NH2:26]

Komponenten

4

Edukt 2

HCID 12043264(R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineHCID 204431481,4-Dioxane hydrochloride

Produkt 1

HCID 54463364(R)-(-)-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4N HCl-dioxane (10 ml) was added to a solution of (R)-(−)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (5.11 g) in ethanol (15 ml), and the mixture was stirred at 50: for one hour. After allowed to cool, the reaction mixture was concentrated under reduced pressure, the residue was neutralized with saturated aqueous sodium bicarbonate, and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, diisopropyl ether was added to crystals so precipitated, washed, and collected by filtration. This was recrystallized from a mixed solvent of ethanol and diisopropyl ether, to thereby obtain 2.1 g of the titled compound.

Aufarbeitung

  1. temperatureto cool
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, diisopropyl ether
  7. additionwas added to crystals
  8. customso precipitated
  9. washwashed
  10. filtrationcollected by filtration
  11. customThis was recrystallized from a mixed solvent of ethanol and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d7532758beb04a758d4504a5640d132e
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239131B1

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