HCID 54378637, compound → HCID 53652743, compound

HRID 375282Notes

Reaction equation

HRID 375282 reaction equation
[C:1]([CH2:5][C:6]([NH:8][N:9]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH:11]([N:28]=[N+]=[N-])[C:10]1=[O:31])=[O:7])([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]([CH2:5][C:6]([NH:8][N:9]1[CH:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH:11]([NH2:28])[C:10]1=[O:31])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 1

HCID 54378637HCID 54378637, compound

Product 1

HCID 53652743HCID 53652743, compound

Reagents, catalysts & solvents 6

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

Procedure

A solution of 1.09 g (2.60 mmol) 1-(t-butylacetamido)-3-azido-5,7-diphenylhexahydroazepin-2-one in 30 mL ethanol and 15 mL methylene chloride was hydrogenated at 42 psi in the presence of 0.40 g 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 30% methanol in ethyl acetate as eluant to afford 300 mg (29%) of the less polar diastereomer as an oil and 420 mg (41%) of the more polar diastereomer as an oil.

Workup

  1. filtrationIt was filtered through Celite with ethanol and methylene chloride
  2. customevaporated
  3. customchromatographed on silica gel using 30% methanol in ethyl acetate as eluant
  4. customto afford 300 mg (29%) of the less polar diastereomer as an oil and 420 mg (41%) of the more polar diastereomer as an oil

Sources & evidence

ORD record
ord-d5a49fc567be4958b3b7028bb4ef1fb4
Source dataset
uspto-grants-1996_01
Patent number
US05484917

Reaction notes

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