HCID 22405512, compound → HCID 10391657, compound

HRID 441180Notes

Reaction equation

HRID 441180 reaction equation
C(OC([NH:11][C:12]1[C:13](=[O:45])[N:14]([CH2:24][C:25]([NH:27][CH:28]([CH:42]([CH3:44])[CH3:43])[CH:29]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C:30]([F:33])([F:32])[F:31])=[O:26])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)=O)C1C=CC=CC=1>O1CCCC1.[Pd]>[NH2:11][C:12]1[C:13](=[O:45])[N:14]([CH2:24][C:25]([NH:27][CH:28]([CH:42]([CH3:43])[CH3:44])[CH:29]([O:34][Si:35]([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36])[C:30]([F:33])([F:31])[F:32])=[O:26])[C:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 22405512HCID 22405512, compound

Product 1

HCID 10391657HCID 10391657, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3-benzyloxycarbonylamino-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (2.41 g) in dry tetrahydrofuran (8 mL) was added 10% (w/w) palladium-on-carbon (0.50 g) in dry tetrahydrofuran (8 mL) under nitrogen. This mixture was stirred under hydrogen at atmospheric pressure for 5 h. The catalyst was removed by filtration through a plug of diatomaceous earth and the plug was washed with ethanol. The filtrate was evaporated and dried under vacuum to give 2-(3-amino-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (1.78 g); TLC: Rf =0.06, ethyl acetate:dichloromethane (6:94); MS: m/z=512(M+1).

Workup

  1. customThe catalyst was removed by filtration through a plug of diatomaceous earth
  2. washthe plug was washed with ethanol
  3. customThe filtrate was evaporated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5ea5e202eadc492e89767d9193ff697f
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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