(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 1780290Notes

Reaction equation

HRID 1780290 reaction equation
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]

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6b10ef9aabce442da2d4060f49c5894a
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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