N-(t-butyl)-2-oxo-3-azido-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amide → N-(t-Butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amide

HRID 429723Notes

Reaction equation

HRID 429723 reaction equation
[C:1]([NH:5][C:6](=[O:32])[CH2:7][N:8]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:11][CH:10]([N:28]=[N+]=[N-])[C:9]1=[O:31])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(Cl)Cl.[Pd]>[C:1]([NH:5][C:6](=[O:32])[CH2:7][N:8]1[CH:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][CH:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:11][CH:10]([NH2:28])[C:9]1=[O:31])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 15908913N-(t-butyl)-2-oxo-3-azido-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amide

Product 1

HCID 15908914N-(t-Butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amideYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 13.7 grams (31.6 mmol) N-(t-Butyl)-2-oxo-3-azido-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amide in 120 mL ethanol and 60 mL methylene chloride was hydrogenated at 42 p.s.i. in the presence of 3.9 grams 10% palladium-on-carbon for 36 hours. It was then filtered through celite with ethanol and methylene chloride, evaporated, and chromatographed on silica gel using 15% and 30% methanol in ethyl acetate as eluent to afford 12.2 grams (95%) of a foam.

Workup

  1. filtrationIt was then filtered through celite with ethanol and methylene chloride
  2. customevaporated
  3. customchromatographed on silica gel using 15% and 30% methanol in ethyl acetate as eluent

Sources & evidence

ORD record
ord-3b1d07c6dfac4aaa8cd052e1a1fe9262
Source dataset
uspto-grants-2001_11
Patent number
US06319915B1

Reaction notes

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