Bromotrichloromethane → HCID 12045143, compound

HRID 748490Notes

Reaction equation

HRID 748490 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]2[S:6][C:7]([S:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:21][CH2:22][CH:23]([C:25]([O:27][CH3:28])=[O:26])[N:24]=4)=[CH:16][C:15]=3[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.BrC(Cl)(Cl)Cl.C1CCN2C(=NCCC2)CC1>ClCCl>[F:1][C:2]1[CH:34]=[CH:33][C:5]2[S:6][C:7]([S:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:21][CH:22]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[N:24]=4)=[CH:16][C:15]=3[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:11])=[O:12])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12045142HCID 12045142, compound

Product 1

HCID 12045143HCID 12045143, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into 40 mL of dichloromethane was dissolved 1.10 g of Compound 22, followed by addition of 498 mg of bromotrichloromethane at −20° C. Further, 700 mg of DBU was added dropwise at the same temperature and the whole was stirred at the same temperature for 5 minutes and then warmed to 0° C., followed by 3.5 hours of stirring. After confirmation of disappearance of the starting material, the reaction was terminated by adding saturated aqueous sodium hydrogen carbonate solution at 0° C., followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1) to obtain 597 mg of the title compound as colorless powder.

Workup

  1. waitfollowed by 3.5 hours
  2. stirringof stirring
  3. customAfter confirmation of disappearance of the starting material, the reaction was terminated
  4. additionby adding saturated aqueous sodium hydrogen carbonate solution at 0° C.
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1)

Sources & evidence

ORD record
ord-6e3df9e933c54a38a81bcf4bda603acb
Source dataset
uspto-grants-2008_07
Patent number
US07399781B2

Reaction notes

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