(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

Reaction equation

HRID 1979465 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d7532758beb04a758d4504a5640d132e
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Linked notes

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