Dimethylformamide → HCID 67232137, compound

Temperature

5 °C

To a solution of 4-fluorocinnamic acid (85 g) and DMF (2.5 mL) in THF (850 mL) was added dropwise oxalyl chloride (97.4 g) at 5° C. over 10 min, and the mixture was stirred at 5° C. for 1 hr. The mixture was concentrated under reduced pressure, and the residue was suspended in THF (300 mL). This suspension was added dropwise at 5° C. to a mixture of (4R)-4-benzyl-1,3-oxazolidin-2-one (100 g), triethylamine (259 g), lithium chloride (108 g) and THF (850 mL) over 30 min, and the mixture was stirred at room temperature for 1 hr. The mixture was poured into water (850 mL), and the mixture was extracted with ethyl acetate (500 mL), washed with saturated aqueous ammonium chloride solution (500 mL) and saturated brine (500 mL), dried and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/IPE to give (4R)-4-benzyl-3-[(2E)-3-(4-fluorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one (134 g, 80%) as a white powder.

1. concentrationThe mixture was concentrated under reduced pressure
2. additionThis suspension was added dropwise at 5° C. to a mixture of (4R)-4-benzyl-1,3-oxazolidin-2-one (100 g), triethylamine (259 g), lithium chloride (108 g) and THF (850 mL) over 30 min
3. stirringthe mixture was stirred at room temperature for 1 hr
4. additionThe mixture was poured into water (850 mL)
5. extractionthe mixture was extracted with ethyl acetate (500 mL)
6. washwashed with saturated aqueous ammonium chloride solution (500 mL) and saturated brine (500 mL)
7. customdried
8. concentrationconcentrated under reduced pressure
9. customThe residue was recrystallized from ethyl acetate/IPE

ORD record

ord-f0353a0cf42e4dc79d400250f6a1fa89

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592454B2