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(4S)-1-[(2S,3S)-3-(N,N-Dibenzylamino)-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide → (4S)-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide

HRID 1780290
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인쇄 미리보기

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HRID 1780290 반응식
C([N:8]([C@@H:16]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@H:17]([OH:33])[C:18]([N:20]1[CH2:31][C@@H:30]([Cl:32])[CH2:29][C@H:21]1[C:22]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19])CC1C=CC=CC=1)C1C=CC=CC=1>C(O)=O.CO.[Pd]>[NH2:8][C@@H:16]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@H:17]([OH:33])[C:18]([N:20]1[CH2:31][C@@H:30]([Cl:32])[CH2:29][C@H:21]1[C:22]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 1

HCID 70049826(4S)-1-[(2S,3S)-3-(N,N-Dibenzylamino)-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide

생성물 1

HCID 22872716(4S)-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide수율 96.4%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 284Formic Acid용매HCID 887Methanol
용매

실험 절차

A solution of 20.0 g (35.6 mmol) of (4S)-1-[(2S,3S)-3-(N,N-dibenzylamino)-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide dissolved in 200 ml of a 4.5% by volume solution of formic acid in methanol was stirred in the presence of 3 g of palladium black at room temperature for 3 hours and then at 40° C. for 2 hours. At the end of this time, the catalyst was removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was then diluted with ethyl acetate. The diluted solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in benzene. Hexane was added to the resulting solution, to obtain 13.1 g of the title compound as a colorless powder, melting at 126°-130° C.

후처리

  1. customAt the end of this time, the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  3. additionThe concentrate was then diluted with ethyl acetate
  4. washThe diluted solution was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. dissolutionthe resulting residue was dissolved in benzene
  8. additionHexane was added to the resulting solution

출처 및 근거

ORD 기록
ord-6b10ef9aabce442da2d4060f49c5894a
출처 데이터셋
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05629406

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