Boron tribromide → HCID 178461488, compound

HRID 604690Notes

Reaction equation

HRID 604690 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([O:26]C)=[N:24][CH:23]=[CH:22][N:21]=3)[C@H:14]2[CH3:28])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([OH:26])=[N:24][CH:23]=[CH:22][N:21]=3)[C@H:14]2[CH3:28])[CH:4]=[C:3]([C:2]([F:29])([F:1])[F:30])[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86627640HCID 86627640, compound

Product 1

HCID 178461488HCID 178461488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) mixture of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-methoxypyrazin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (1000 mg, 2.297 mmol) in CH2Cl2 (3 mL) was added BBr3 (11.49 mL, 11.49 mmol) dropwise through an addition funnel. The resulting mixture was stirred cold (−78° C.) for 1 h then allowed to warmed to room temperature overnight. The reaction was not completed after overnight stirring. The reaction mixture was stirred at room temperature for 4 more days and LCMS of aliquot indicated completion of reaction. The crude mixture was poured into crushed ice. The resulting organic layer was separated. The aqueous phase was back extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered and evaporated to give a glass. This glass was purified by flash chromatography (SiO2, Biotage 40M cartridge). The column was eluted with a EtOAc/CH2Cl2 gradient mixture (0% to 100%). Related fractions were pooled and evaporated to afford a yellow solid as the titled compound. LCMS calc.=421.09; found=421.95 (M+H)+.

Workup

  1. temperatureto warmed to room temperature overnight
  2. waitThe reaction was not completed after overnight
  3. stirringstirring
  4. stirringThe reaction mixture was stirred at room temperature for 4 more days and LCMS of aliquot indicated completion of reaction
  5. custominto crushed ice
  6. customThe resulting organic layer was separated
  7. extractionThe aqueous phase was back extracted with EtOAc
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give a glass
  12. customThis glass was purified by flash chromatography (SiO2, Biotage 40M cartridge)
  13. washThe column was eluted with a EtOAc/CH2Cl2 gradient mixture (0% to 100%)
  14. customevaporated

Sources & evidence

ORD record
ord-b6f64b7930c54844a8cacfe1d8b22517
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

Loading…