Bromopinacolone → 1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1979439
[H-].[Na+].[O:3]=[C:4]1[NH:10][C:9]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:8]=2[N:7]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:6][CH:5]1[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Br[CH2:31][C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])=[O:33]>CN(C)C=O>[C:34]([C:32]([CH2:31][N:10]1[C:9]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:8]=2[N:7]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:6][CH:5]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:4]1=[O:3])=[O:33])([CH3:37])([CH3:36])[CH3:35]

Komponenten

5

Edukt 3

HCID 21642BromopinacoloneHCID 24758Sodium hydrideHCID 212017342-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 212015981-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

60% Sodium hydride (53 mg) was suspended in anhydrous N,N-dimethylformamide (5 ml), under ice-cooling 2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (410 mg) was added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, bromomethyl-tert-butyl ketone (217 mg) was added to the mixture under ice-cooling, the mixture was stirred at room temperature for 30 minutes. Ice-water was added to the reaction mixture, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, to thereby 517 mg of the title compound (Yield: 100%).

Aufarbeitung

  1. additionwas added
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6c616ef7cb954cfaa5810b147ee9530d
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239131B1

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