Cyclohexanone → (R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 352375

Reaktionsgleichung

[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][CH:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[C:21]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)(=O)C.[C].[Pd]>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:4][C@H:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 52.5 °C

Versuchsvorschrift

In 1.2 g of acetic acid were dissolved 1.39 g of 2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine and 3.9 g of cyclohexanone. To the resulting solution was added 302 mg of 10% palladium carbon. Under a hydrogen pressure of 10 kg/cm2, the mixture was stirred at 50 to 55° C. for 12 hours. After the reaction mixture was cooled to room temperature, the reaction mixture was filtered through Celite. Water was added to the filtrate and crystals so precipitated were collected by filtration with suction. The resulting crystals were recrystallized from a mixed solvent of ethanol and water, whereby 1.63 g of the title compound was obtained.

Aufarbeitung

temperatureAfter the reaction mixture was cooled to room temperature
filtrationthe reaction mixture was filtered through Celite
additionWater was added to the filtrate and crystals
customso precipitated
filtrationwere collected by filtration with suction
customThe resulting crystals were recrystallized from a mixed solvent of ethanol and water

Quellen und Nachweise

ORD-Eintrag: ord-c0af054623e5427b990146935d0c2a8e
Quelldatensatz: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06747022B2

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