(+/-)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahy dro-2H-1,5-benzodiazepine → 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1698768Notes

Reaction equation

HRID 1698768 reaction equation
[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][CH:10]([NH:25]C(OC(C)(C)C)=O)[C:9]1=[O:33])=[O:6])([CH3:4])([CH3:3])[CH3:2]>C(O)C.Cl.O1CCOCC1>[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][CH:10]([NH2:25])[C:9]1=[O:33])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 15490834(+/-)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahy dro-2H-1,5-benzodiazepine

Product 1

HCID 154908351-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (±)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahy dro-2H-1,5-benzodiazepine (2.2 g) in ethanol (10 mL), 4 N hydrochloric acid-dioxane solution (10 mL) was added. The resulting mixture was stirred at 50° C. for 30 minutes. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the residue for neutralization. The resultant mixture was extracted with methylene chloride. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the residue for crystallization. Crystals so precipitated were collected by filtration, whereby the title compound (1.1 g) was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue for neutralization
  3. extractionThe resultant mixture was extracted with methylene chloride
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  7. additionwas added to the residue for crystallization
  8. customCrystals so precipitated
  9. filtrationwere collected by filtration, whereby the title compound (1.1 g)
  10. customwas obtained

Sources & evidence

ORD record
ord-dc3c65900a95404b945c52f8dbb838ec
Source dataset
uspto-grants-2002_02
Patent number
US06344452B1

Reaction notes

Loading…