Potassium Carbonate → HCID 21201756, compound

HRID 1979477Notes

Reaction equation

HRID 1979477 reaction equation
Br[CH2:2][C:3]([C:5]([CH3:8])([CH3:7])[CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].[O:15]=[C:16]1[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:18][CH:17]1[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.[I-].[K+]>[C:5]([C:3]([CH2:2][N:22]1[C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:18][CH:17]([NH:32][C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[C:16]1=[O:15])=[O:4])([CH3:8])([CH3:7])[CH3:6]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 21201602HCID 21201602, compound

Product 1

HCID 21201756HCID 21201756, compoundYield 75.8%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

Bromomethyl tert-butylketone (684 mg), potassium iodide (26.4 mg), tetra n-butylammonium bromide (30.8 mg) and potassium carbonate (528 mg) were added successively to a solution of 2-oxo-3-tert-butoxycarbonylamino-5-cyclopentyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.1 g) in N,N-dimethylformamide (30 ml), the mixture was stirred at room temperature for 2 hours. Ice-water was added to the reaction mixture, 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 n-hexane was added to the residue for crystallization, collected by filtration, to thereby obtain 1.07 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe resultant mixture was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure, and n-hexane
  5. additionwas added to the residue for crystallization
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-886e26507b234b12b9fe13014a4e2a55
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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