Ethyl Acetate → (R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 352383

反応式

HRID 352383 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][C@H:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH:21]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]CC=1.C(OCC)(=O)C>C1(=O)CCCCC1.[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]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:21]=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

6

反応物 3

HCID 8857Ethyl AcetateHCID 136091-CycloocteneHCID 12988641(R)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

生成物 1

HCID 12988647(R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine収率 50.2%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 7967Cyclohexanone溶媒

反応条件

温度
145 °C

実験手順

To a solution of 5 g of (R)-(+)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine in 25 ml of cyclohexanone were added 5.96 g of cyclooctene and 0.5 g of 10% palladium carbon. The mixture was stirred at the internal temperature of 145° C. for 2.5 hours. After the reaction mixture was cooled to room temperature, 20 ml of ethyl acetate was added. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was crystallized by adding thereto diisopropyl ether and n-hexane and the resulting crystals were collected by filtration, whereby 3.2 g of the title compound was obtained.

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was crystallized
  5. additionby adding
  6. filtrationdiisopropyl ether and n-hexane and the resulting crystals were collected by filtration

出典と根拠

ORDレコード
ord-cd97a41839564bccb51d26a6e8f7ae1f
出典データセット
uspto-grants-2004_06
特許番号
US06747022B2

関連ノート

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