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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
ノート
印刷プレビュー

反応式

HRID 1780290 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 284Formic Acid溶媒HCID 887Methanol
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6b10ef9aabce442da2d4060f49c5894a
出典データセット
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05629406

反応ノート

読み込み中…

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