Sodium Bicarbonate → HCID 53793513, compound

HRID 1979479Notes

Reaction equation

C(=O)(O)[O-].[Na+].Br[CH:7]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8]1.[O:15]=[C:16]1[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[NH:19][CH2:18][CH:17]1[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C)C=O>[O:15]=[C:16]1[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]([CH:7]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8]2)[CH2:18][CH:17]1[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium bicarbonate (606 mg) and 3-bromocyclooctene (1.36 g) were added to a solution of 2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1 g) in N,N-dimethylformamide (20 ml), the mixture was stirred overnight at 80° C. After the reaction mixture was allowed to cool, ice-water was added thereto, extracted with ethyl acetate, the organic layer was washed with saturated brine. The resultant mixture was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and diisopropyl ether was added to the residue for crystallization, and collected by filtration, to thereby obtain 615 mg of the title compound as the mixture of diastereomer compounds.

Workup

temperatureto cool
extractionextracted with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialThe resultant mixture was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure, and diisopropyl ether
additionwas added to the residue for crystallization
filtrationcollected by filtration

Sources & evidence

ORD record: ord-b7eb6116ec344084b3f41a227c168e48
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239131B1

Reaction notes

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