Benzoyl Peroxide → HCID 67483176, compound

HRID 1816185Notes

Reaction equation

HRID 1816185 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[N:20]=2)=[CH:10][CH:9]=1.BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Li+].[Li+].[Br-].[Li+]>ClC(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[C:15]([C:32]2[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=2)[C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:30])([F:31])[F:29])=[CH:23][CH:22]=3)[N:20]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 7187Benzoyl PeroxideHCID 11125Lithium CarbonateHCID 67184N-bromobutanimideHCID 82050Lithium BromideHCID 42637032HCID 42637032, compound

Product 1

HCID 67483176HCID 67483176, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 3-(4-{2-(4-chlorophenyl)-2-[4-(4-trifluoromethoxyphenyl)thiazol-2-yl]ethyl}benzoylamino)propionic acid methyl ester (the product from step 5) (0.15 g, 0.255 mmol), N-bromosuccinimide (50 mg, 0.28 mmol) in tetrachloromethane (9 mL) was added a catalytic amount of dibenzoylperoxide and the resulting mixture was stirred at reflux for 4 hours. After cooling, the mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with water (2×) and brine, dried over MgSO4, treated with active carbon, filtered and concentrated in vacuo. The residue (157 mg) was dissolved in DMF (5 mL) and lithium carbonate (21 mg, 0.28 mmol) and lithium bromide (24 mg, 0.28 mmol) were added and the resulting mixture was refluxed for 3.5 hours. After cooling, the mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with water (3×) treated with active carbon, dried (MgSO4) and concentrated in vacuo. The residue (56 mg) was purified by HPLC to afford 14 mg of 3-(4-{2-(4-chlorophenyl)-2-[4-(4-trifluoromethoxyphenyl)-thiazol-2-yl]vinyl}benzoylamino)propionic acid methyl ester.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phases were washed with water (2×) and brine
  7. dry with materialdried over MgSO4
  8. additiontreated with active carbon
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. dissolutionThe residue (157 mg) was dissolved in DMF (5 mL)
  12. temperaturethe resulting mixture was refluxed for 3.5 hours
  13. temperatureAfter cooling
  14. customthe mixture was partitioned between water and ethyl acetate
  15. extractionThe aqueous phase was extracted with ethyl acetate
  16. washthe combined organic phases were washed with water (3×)
  17. additiontreated with active carbon
  18. dry with materialdried (MgSO4)
  19. concentrationconcentrated in vacuo
  20. customThe residue (56 mg) was purified by HPLC

Sources & evidence

ORD record
ord-f12b88660d54474ba11ea51b499504d6
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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