N-bromobutanimide → HCID 9934776, compound

HRID 1057371Notes

Reaction equation

HRID 1057371 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[N:10]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[C:9]1=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:37])C(=O)C1>C(O)(=O)C.C(Cl)(Cl)Cl.C(Cl)Cl>[Br:37][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:11]2[N:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[C:9](=[O:29])[CH:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14][CH2:13][C:12]=2[CH:15]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 10272253HCID 10272253, compound

Product 1

HCID 9934776HCID 9934776, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-tert-butoxycarbonyl-1-(3-fluorobenzyl)-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (1.00 g, 2.503 mmol) and NBS (0.49 g, 2.754 mmol) in acetic acid (0.8 mL) and chloroform (8 mL) was heated at reflux for 4 hrs. The reaction mixture was allowed to cool to room temperature, diluted with DCM (30 mL), washed with saturated aqueous sodium bicarbonate solution, dried over Na2SO4. Filtration and evaporation of the organic layer gave a solid residue, which was purified by flash chromatography on silica column eluted with ethyl acetate/n-hexane (25% of ethyl acetate in n-hexane). The title compound was obtained as a white powder (0.400 g, 33%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hrs
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation of the organic layer
  6. customgave a solid residue, which
  7. customwas purified by flash chromatography on silica column
  8. washeluted with ethyl acetate/n-hexane (25% of ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-75244df0db394dee8cafe2beb67b0b29
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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