Dimethylformamide → HCID 60031521, compound

To a mixed solution of (2E)-3-(4-chlorophenyl)prop-2-enoic acid (30.0 g) in THF (350 mL) and DMF (0.90 mL) was slowly added oxalyl chloride (21.6 mL) at 5° C., and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in THF (150 mL). This THF solution was added to a suspension of (R)-4-benzyloxazolidin-2-one (31.0 g), triethylamine (114 mL) and lithium chloride (34.8 g) in THF (350 mL) at 5° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic layer was washed with 10% aqueous citric acid solution and saturated brine, dried and concentrated under reduced pressure to give (4R)-4-benzyl-3-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one (40.0 g, 71%) as a white powder.

1. customat 5° C.
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. dissolutionthe residue was dissolved in THF (150 mL)
4. additionThis THF solution was added to a suspension of (R)-4-benzyloxazolidin-2-one (31.0 g), triethylamine (114 mL) and lithium chloride (34.8 g) in THF (350 mL) at 5° C.
5. stirringthe mixture was stirred at room temperature for 14 hr
6. concentrationThe reaction mixture was concentrated under reduced pressure, and water and ethyl acetate
7. additionwere added to the residue
8. washThe organic layer was washed with 10% aqueous citric acid solution and saturated brine
9. customdried
10. concentrationconcentrated under reduced pressure

ORD record

ord-854bd40db6d846a8987a1d9cc10d7628

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592454B2