HCID 70043047, compound → HCID 70042834, compound

HRID 441204Notes

Reaction equation

HRID 441204 reaction equation
C([O:8][C:9]([CH:11]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:12]([NH:14][C:15]1[C:16](=[O:41])[N:17]([CH2:27][C:28]([NH:30][CH:31]([CH:38]([CH3:40])[CH3:39])[C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])=[O:29])[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)=[O:13])=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:9]([CH:11]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:12]([NH:14][C:15]1[C:16](=[O:41])[N:17]([CH2:27][C:28]([NH:30][CH:31]([CH:38]([CH3:39])[CH3:40])[C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])=[O:29])[C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)=[O:13])([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 70043047HCID 70043047, compound

Product 1

HCID 70042834HCID 70042834, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2-[3-(2-Benzyloxycarbonylphenylacetylamino)-2-oxo-6-phenyl-1,2-dihydo-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.6 g) in methanol (50 mL) was added 10% (w/w) palladium on carbon (0.2 g), and the mixture was shaken under a hydrogen atmosphere (3.4 bar) for 3 h. The catalyst was filtered and the solvent evaporated to give a solid which was chromatographed, eluting with methanol:dichloromethane (gradient, 2:98 to 10:90), to give the title compound (0.5 g); TLC: Rf =0.25, methanol:dichloromethane (10:90); MS: m/z=588(M+1).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent evaporated
  3. customto give a solid which
  4. customwas chromatographed
  5. washeluting with methanol

Sources & evidence

ORD record
ord-fe97e8ef2e9d451e9b0f883b346b18c5
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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