4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester → ethyl 4-[(2S)-2-amino-5-tert-butoxy-5-oxopentanoyl]piperazine-1-carboxylate

HRID 1970418Notes

Reaction equation

HRID 1970418 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:34])[C@@H:13]([NH:23]C(OCC2C=CC=CC=2)=O)[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:34])[C@@H:13]([NH2:23])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 666517784-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 66651766ethyl 4-[(2S)-2-amino-5-tert-butoxy-5-oxopentanoyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 20.9 g 4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 120 ml ethanol were added 2.0 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 not further purified. Yield: 13.6 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-6c7b290044984afd83b737fcf78bc1a0
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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