2-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(5-methyl-hexanoyl)-piperazine-1-carboxylic acid tert-butyl ester → 2-(R)-(2-(R)-Amino-1-(S)-hydroxy-3-phenyl-propyl)-4-(5-methylhexanoyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436514Notes

Reaction equation

HRID 1436514 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:10][C@@H:9]1[C@@H:22]([OH:45])[C@H:23]([N:31]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:10][C@@H:9]1[C@@H:22]([OH:45])[C@H:23]([NH2:31])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 866153782-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(5-methyl-hexanoyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 690176622-(R)-(2-(R)-Amino-1-(S)-hydroxy-3-phenyl-propyl)-4-(5-methylhexanoyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 2-(R)-[2-(R)-(Benzhydrylideneamino)-1-(S)-hydroxy-3-phenyl-propyl]-4-(5-methylhexanoyl)-piperazine-1-carboxylic acid tert-butyl ester (103 mg, 0.17 mmol) in 2 ml of methanol and add palladium (10% on C, 30 mg). Stir under 1 atmosphere of H2 for 24 h and filter through celite, eluting with methanol. Concentrate to dryness to provide the title compound.

Workup

  1. filtrationfilter through celite
  2. washeluting with methanol
  3. concentrationConcentrate to dryness

Sources & evidence

ORD record
ord-4e9b9a9de5d14ad2a6c88b542f6a7030
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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