Sodium Bicarbonate → HCID 21201956, compound

HRID 1979478Notes

Reaction equation

HRID 1979478 reaction equation
C(=O)(O)[O-].[Na+].Br[CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8]1.[O:14]=[C:15]1[NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[NH:18][CH2:17][CH:16]1[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>CN(C)C=O>[O:14]=[C:15]1[NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]([CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8]2)[CH2:17][CH:16]1[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 124538813-Bromocyclohept-1-eneHCID 15490831HCID 15490831, compound

Product 1

HCID 21201956HCID 21201956, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium bicarbonate (1.6 g) and 3-bromocycloheptene (3.33 g) were added to a solution of 2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (2.77 g) in N,N-dimethylformamide (20 ml), the mixture was stirred at 50° C. for one hour. 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 the residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:2), diisopropyl ether was added to the residue for crystallization, and collected by filtration, to thereby obtain 2.1 g of the title compound as the mixture of diastereomer compounds.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialThe resultant mixture was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:2), diisopropyl ether
  7. additionwas added to the residue for crystallization
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3943b9e952f14b899cd1cad78c1dfa5b
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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