(S,E)-3-(pent-2-enoyl)-4-phenyloxazolidin-2-one → (S)-4-phenyl-3-((R)-3-phenyl-pentanoyl)-oxazolidin-2-one

Temperature

-10 °C

To a suspension of copper (I) bromide dimethyl sulfide complex (12.4 g, 60.6 mmol) in dry tetrahydrofuran (150 mL) at −10° C. was added phenyl magnesium chloride solution (30.3 mL, 60.6 mmol, 2 M in tetrahydrofuran). The reaction mixture was stirred at −10° C. for 1 hour, then a solution of (S)-3-((E)-pent-2-enoyl)-4-phenyl-oxazolidin-2-one (9.9 g, 40.4 mmol) in tetrahydrofuran (100 mL) was added dropwise via cannula. The reaction mixture was stirred at −10° C. for 0.5 hours, then at room temperature for 2 hours. The mixture was quenched with saturated aqueous ammonium chloride solution (150 mL), concentrated under reduced pressure to half of its volume. The mixture was extracted with ethyl acetate (2×250 mL). The organic layer was separated, combined and dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give (S)-4-phenyl-3-((R)-3-phenyl-pentanoyl)-oxazolidin-2-one as a colorless oil which solidified on standing at room temperature (9.56 g, 73%).

1. stirringThe reaction mixture was stirred at −10° C. for 0.5 hours
2. waitat room temperature for 2 hours
3. customThe mixture was quenched with saturated aqueous ammonium chloride solution (150 mL)
4. concentrationconcentrated under reduced pressure to half of its volume
5. extractionThe mixture was extracted with ethyl acetate (2×250 mL)
6. customThe organic layer was separated
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by chromatography over silica gel
10. washeluted with 2:1 ethyl acetate/hexanes

ORD record

ord-d27fbc678b364e1bade21ff327dbf0a5

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07427635B2