Carbon Tetrachloride → HCID 9944801, compound

HRID 1057367Notes

Reaction equation

HRID 1057367 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][CH3:22])[C:9]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N(Br)C(=O)C1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.C(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[C:1]([O:5][C:6]([CH:8]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[N:10]([CH2:21][CH3:22])[C:9]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 9836705HCID 9836705, compound

Product 1

HCID 9944801HCID 9944801, compoundYield 125.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A three-necked flask, equipped with reflux condenser, was charged with 3-tert-butoxycarbonyl-1-ethyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (4.0 g, 12.52 mmol), NBS (2.452 g, 13.76 mmol), N,O-bis(trimethylsilyl)acetamide (1.712 mL, 6.88 mmol), BPO (ca. 20 mg) and carbon tetrachloride (160 mL). The suspension was heated to reflux when another portion (ca. 20 mg) of BPO was added. After being refluxed for 3 hrs, the reaction mixture was diluted with DCM (100 mL), washed with water and dried over Na2SO4. The reaction was repeated for another 5 times and the combined organic layers were filtered and evaporated. The residue was repeatedly purified by flash chromatograghy on silica column eluted by ethyl acetate/DCM (2.5%) or ethyl acetate/hexane (20%). The crystal residue was further washed with ethyl acetate/hexane (20%) and dried in vacuum, giving the title compound (4.970 g, 21%) as white crystal.

Workup

  1. customA three-necked flask, equipped
  2. temperaturewith reflux condenser
  3. temperatureThe suspension was heated
  4. temperatureto reflux when another portion (ca. 20 mg) of BPO
  5. additionwas added
  6. temperatureAfter being refluxed for 3 hrs
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. filtrationthe combined organic layers were filtered
  10. customevaporated
  11. customThe residue was repeatedly purified by flash chromatograghy on silica column
  12. washeluted by ethyl acetate/DCM (2.5%) or ethyl acetate/hexane (20%)
  13. washThe crystal residue was further washed with ethyl acetate/hexane (20%)
  14. customdried in vacuum

Sources & evidence

ORD record
ord-bc87cdb6aec34bf39328b80d479caad0
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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