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 53134Notes

Reaction equation

HRID 53134 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.CO.C(OCC)(=O)C.[Pd].[H+].[H+].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[K+].[I-].[Pt]>[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

8

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 6

HCID 23938PalladiumCatalystHCID 170165iodoplatinateCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

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 psi in the presence of 3.9 grams 10% palladium-on-carbon for 36 hours. The reaction showed Rf =0.30/0.15 iodoplatinate positive, in 30% methanol in ethyl acetate. It was filtered through Celite with ethanol and methylene chloride, evaporated, and chromatographed on silica gel using 15% and 30% methanol in ethyl acetate as eluant to afford 12.2 grams (95%) of a foam. 1H-NMR (δ, CDCl3): 1.13 (singlet, 9H), 2.0-2.5 and 3.9 (multiplets, 6H), 2.28 (s, 3H), 3.4 (m, 1H), 4.7 (m, 2H), 5.18 (d, J=10, 1H), 5.94 (broad singlet, 1H, NH), 7.0-7.3 (m, 9H). 13C-NMR (δ, CDCl3): 19.6, 28.6, 37.3, 38.7, 40.8, 48.2, 51.1, 53.5, 60.9, 126.0, 126.4, 128.6, 128.8, 129.8, 130.6, 134.8, 138.1, 143.0, 168.0, 174.1.

Workup

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

Sources & evidence

ORD record
ord-2dd1f6d231904b3f848a1787236f03bc
Source dataset
uspto-grants-1997_04
Patent number
US05618811

Reaction notes

Loading…