3-Bromocyclohexene → (3R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979464

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.C(=O)(O)[O-].[Na+].[O:13]=[C:14]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[NH:17][CH2:16][C@H:15]1[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CN(C)C=O>[O:13]=[C:14]1[NH:20][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:17]([CH:18]2[CH2:24][CH2:23][CH2:22][CH:21]=[CH:19]2)[CH2:16][C@H:15]1[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]

Participants

Conditions

Temperature: 50 °C

Procedure

3-Bromocyclohexene (7.06 g) and sodium bicarbonate (3.68 g) were added to a solution of (R)-(+)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (6.08 g) in anhydrous N,N-dimethylformamide (50 ml), and the mixture was stirred at 50° C. for one hour. The reaction mixture was allowed to cool, ice-water was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure,the residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:3), to thereby obtain 7.84 g of the titled compound.

Workup

temperatureto cool
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record: ord-c75f7bbd45844e82a5bc132c9d783059
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239131B1

Linked notes

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