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

HRID 352375

반응식

HRID 352375 반응식
[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]

참가 물질

5

반응물 2

HCID 7967CyclohexanoneHCID 15490831HCID 15490831, 화합물

생성물 1

HCID 12043264(R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine수율 90.5%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 176Acetic Acid용매

반응 조건

온도
52.5 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c0af054623e5427b990146935d0c2a8e
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747022B2

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