Monosodium phosphate → (E)-10-heptyloxy-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-dec-3-en-1-one

Temperature

0 °C

Under a nitrogen atmosphere, (E)-10-heptyloxy-dec-3-enoic acid obtained in Step C-3 (209.7 mg, 0.698 mmol) and a commercially available reagent of (S)-4-isopropyl-5,5-diphenyl-oxazolidine-2-thione (207.5 mg, 0.698 mmol) were dissolved in dichloromethane (3.13 mL), and the mixture was cooled to 0° C. While maintaining the temperature at 0° C., N,N-dimethyl-4-aminopyridine (8.5 mg, 0.0698 mmol) and WSCl (173.9 mg, 0.907 mmol) were added in order. The mixture was stirred at 0° C. for 2.0 minutes and at room temperature for 16 hours. To the reaction solution was added an aqueous solution (4.2 mL) of 10% sodium dihydrogen phosphate and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated brine in order, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The resulting residue was then purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.6) to obtain (E)-10-heptyloxy-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-dec-3-en-1-one (No. 6804254; 336.2 mg, 3 steps, 75% yield).

1. temperatureWhile maintaining the temperature at 0° C.
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with water
4. dry with materiala saturated brine in order, dried over anhydrous sodium sulfate
5. filtrationfiltered
6. distillationThe solvent was distilled off
7. customThe resulting residue was then purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.6)

ORD record

ord-943bb56491f747fdb601900165a2def6

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2