4-((S)-4-tert-Butoxycarbonyl-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid benzyl ester → (S)-4-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-5-oxo-5-piperazin-1-yl-pentanoic acid tert-butyl ester

HRID 1908649Notes

Reaction equation

HRID 1908649 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:50])[C@@H:18]([NH:28][C:29]([C:31]2[CH:35]=[C:34]([O:36][CH2:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[N:33]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:32]=2)=[O:30])[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:24]([O:23][C:21](=[O:22])[CH2:20][CH2:19][C@H:18]([NH:28][C:29]([C:31]1[CH:35]=[C:34]([O:36][CH2:37][C:38](=[O:43])[C:39]([CH3:40])([CH3:41])[CH3:42])[N:33]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:32]=1)=[O:30])[C:17](=[O:50])[N:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([CH3:25])([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 669201124-((S)-4-tert-Butoxycarbonyl-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 66920033(S)-4-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-5-oxo-5-piperazin-1-yl-pentanoic acid tert-butyl esterYield 115.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4.4 g 4-((S)-4-tert-Butoxycarbonyl-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid benzyl ester in 40 ml ethanol were added 0.9 g Pd/C (10%) and the suspension stirred under an atmosphere of hydrogen (3 bar) for 24 h. It was filtrated, washed with ethanol and the solvent evaporated to give the title compound as colorless oil (4.1 g).

Workup

  1. filtrationIt was filtrated
  2. washwashed with ethanol
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-5cafd9a65cf94b8081a84c43cd1b8d49
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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