Bromopinacolone → HCID 53718259, compound

HRID 1979487Notes

Reaction equation

HRID 1979487 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:4][C@H:3]1[NH:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:24]=1)=[O:21].[H-].[Na+].Br[CH2:40][C:41]([C:43]([CH3:46])([CH3:45])[CH3:44])=[O:42]>CN(C)C=O>[C:43]([C:41]([CH2:40][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:4][C@@H:3]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:24]=2)=[O:21])[C:2]1=[O:1])=[O:42])([CH3:46])([CH3:45])[CH3:44]

Participants

5

Reactant 3

HCID 21642BromopinacoloneHCID 24758Sodium hydrideHCID 53639613HCID 53639613, compound

Product 1

HCID 53718259HCID 53718259, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-(−)-1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylmethylphenyl)urea (4.93 g) was added to a suspension of 60% sodium hydride (440 mg) in anhydrous N,N-dimethylformamide (50 ml) under ice-cooling, the mixture was stirred for one hour. Bromomethyl tert-butylketone (1.97 g) was added thereto, the resultant mixture was stirred at room temperature for one hour, the reaction mixture was poured into ice-water, extracted with ethyl acetate, and the organic layer was washed with saturated brine. After dried over anhydrous sodium sulfate, the mixture was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3), to thereby obtain 5.07 g of the title compound (Yield: 86%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialAfter dried over anhydrous sodium sulfate
  5. customthe mixture was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-1132efbec68341c28a11706c3235d162
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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