HCID 69151040, compound → HCID 69152735, compound

HRID 1744133Notes

Reaction equation

HRID 1744133 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:10]([NH:32][C@H:33]([C:38]([O:40]CC2C=CC(OC)=CC=2)=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:23][CH2:24]3)=[CH:17][CH:18]=2)[C:10]([NH:32][C@H:33]([C:38]([OH:40])=[O:39])[CH2:34][CH:35]([CH3:36])[CH3:37])=[N:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 69151040HCID 69151040, compound

Product 1

HCID 69152735HCID 69152735, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 4-methoxybenzyl N-(1-(tert-butoxycarbonyl)4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucinate (1.14 g, 1.68 mmol) in EtOH (30 mL) was added the catalyst palladium on carbon (10%, 500 mg) and the reaction was stirred under a hydrogen atmosphere overnight. After degassing with nitrogen, CH2Cl2 was added and the reaction mixture was filtered on celite, washed with EtOH, concentrated in vacuo and purified by flash chromatography over silica gel (AcOH/EtOAc/Hex, 1/49/50) to afford N-(1-(tert-butoxycarbonyl)-4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucine.

Workup

  1. customAfter degassing with nitrogen, CH2Cl2
  2. additionwas added
  3. filtrationthe reaction mixture was filtered on celite
  4. washwashed with EtOH
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography over silica gel (AcOH/EtOAc/Hex, 1/49/50)

Sources & evidence

ORD record
ord-47648e10a9494e28bec2f81dd787e0c2
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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