1,4-Dioxane hydrochloride → 1-cyclohexylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979473Notes

Reaction equation

Cl.O1CCOCC1.[CH:8]1([C:14]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:20][CH:19]([NH:34]C(OC(C)(C)C)=O)[C:18]2=[O:42])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C(O)C>[CH:8]1([C:14]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[CH2:20][CH:19]([NH2:34])[C:18]2=[O:42])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 50 °C

Procedure

4N HCl-dioxane (10 ml) was added to a solution of 1-cyclohexylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (500 mg) in ethanol (10 ml), and the mixture was stirred at 50° C. for one hour. The reaction mixture was concentrated under reduced pressure, the residue was neutralized with saturated aqueous sodium bicarbonate, extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, to thereby obtain 400 mg of the title compound.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with methylene chloride
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-34aba31c98cd4ea8aa447ba437a0766f
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239131B1

Reaction notes

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