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

HRID 352375ノート

反応式

HRID 352375 の反応式
[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]

参加物

5

反応物 2

HCID 7967CyclohexanoneHCID 15490831HCID 15490831、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 176Acetic Acid溶媒

反応条件

温度
52.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c0af054623e5427b990146935d0c2a8e
出典データセット
uspto-grants-2004_06
特許番号
US06747022B2

反応ノート

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