Dimethylformamide → (4R)-4-benzyl-3-[(2E)-3-(3,4-dichlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one

To a solution of (2E)-3-(3,4-dichlorophenyl)prop-2-enoic acid (5.0 g) and DMF (178 μL) in THF (115 mL) was added oxalyl chloride (3.98 mL) at room temperature, and the mixture was stirred for 45 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in THF (13.8 mL). The THF solution was added dropwise to a solution of (4R)-4-benzyl-1,3-oxazolidin-2-one (4.48 g), triethylamine (15.9 mL) and LiCl (4.87 g) in THF (115 mL) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with water and brine and dried, and the solvent was evaporated under reduced pressure to give (4R)-4-benzyl-3-[(2E)-3-(3,4-dichlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one (4.22 g, 49%) as a white powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in THF (13.8 mL)
3. additionThe THF solution was added dropwise to a solution of (4R)-4-benzyl-1,3-oxazolidin-2-one (4.48 g), triethylamine (15.9 mL) and LiCl (4.87 g) in THF (115 mL) at 0° C.
4. stirringthe mixture was stirred overnight at room temperature
5. additionThe reaction mixture was poured into water
6. extractionthe resultant product was extracted with ethyl acetate
7. washThe organic layer was washed with water and brine
8. customdried
9. customthe solvent was evaporated under reduced pressure

ORD record

ord-260d271a6c8d4170ae367f8900ecc734

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470816B2