4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester → HCID 45140546, compound

HRID 1970504Notes

Reaction equation

HRID 1970504 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:36])[C@@H:15]([NH:25]C(OCC2C=CC=CC=2)=O)[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]>C(O)C.[Pd]>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:36])[C@@H:15]([NH2:25])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 451403594-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester

Product 1

HCID 45140546HCID 45140546, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 15.8 g 4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester in 60 ml ethanol were added 1.8 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 purified by flash chromatography on silica using dichloro-methane/methanol 90:10 as eluent. Yield: 9.6 g colorless oil.

Workup

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

Sources & evidence

ORD record
ord-179642d7273f44ad8982f4df71f415b7
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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