HCID 54512598, 화합물 → (R)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979463

반응식

HRID 1979463 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[C].[Pd]>[O:11]=[C:10]1[NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH2:13][C@H:9]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

참가 물질

4

반응물 1

HCID 54512598HCID 54512598, 화합물

생성물 1

HCID 12988641(R)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine수율 80%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

10% palladium carbon (1 g) was added to a solution of (R)-(−)-2-tert-butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (7.6 g) in tetrahydrofuran (100 ml), and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hours. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure, to thereby obtain (R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)propionic acid. The residue was dissolved in toluene (100 ml), the solution was refluxed overnight. After allowed to cool, the reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:1), to thereby obtain 5.16 g of the title compound (Yield 80%).

후처리

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in toluene (100 ml)
  4. temperaturethe solution was refluxed overnight
  5. temperatureto cool
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(ethyl acetate:n-hexane=1:1)

출처 및 근거

ORD 기록
ord-687427fe6fb64bada85a3d4ab6f4e89d
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

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