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

HRID 1182676Notes

Reaction equation

HRID 1182676 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]>CCO.[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, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-((S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester (4.00 g, prepared as described in WO2008050301) and Pd/C (5%, 0.42 g) in EtOH (15 mL) was hydrogenated at RT overnight. The reaction mixture was then stirred under H2 overnight. The mixture was filtered through celite and evaporated off. HV drying afforded the desired compound as light brown oil (2.79 g).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated off
  3. customHV drying

Sources & evidence

ORD record
ord-0057e16d2eeb4504bdbacf62e8a0693f
Source dataset
uspto-grants-2014_03
Patent number
US08664203B2

Reaction notes

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