4-((S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyryl)-piperazine-1-carboxylic acid propyl ester → 4-((S)-2-Amino-4,4,4-trifluoro-butyryl)-piperazine-1-carboxylic acid propyl ester

HRID 1970655Notes

Reaction equation

HRID 1970655 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:31])[C@@H:14]([NH:20]C(OCC2C=CC=CC=2)=O)[CH2:15][C:16]([F:19])([F:18])[F:17])[CH2:9][CH2:8]1)=[O:6])[CH2:2][CH3:3]>C(O)C.[Pd]>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:31])[C@@H:14]([NH2:20])[CH2:15][C:16]([F:17])([F:19])[F:18])[CH2:9][CH2:8]1)=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 668549974-((S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyryl)-piperazine-1-carboxylic acid propyl ester

Product 1

HCID 668546174-((S)-2-Amino-4,4,4-trifluoro-butyryl)-piperazine-1-carboxylic acid propyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 170 mg 4-((S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyryl)-piperazine-1-carboxylic acid propyl ester in 20 ml ethanol were added 0.05 g Pd/C (10%) and the suspension stirred under an atmosphere of hydrogen (3 bar) for 12 h. The reaction mixture was filtrated over a plug of Celite, washed with ethanol and concentrated to give the crude product which was used in the subsequent reaction. Yield: 106 mg.

Workup

  1. filtrationThe reaction mixture was filtrated over a plug of Celite
  2. washwashed with ethanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-65167202c37242118506f659f2584110
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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