2-Dimethylaminopyridine → (E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-one

Participants

Reaction Conditions

Reaction Steps

(S)-4-Isopropyl-5,5-diphenyl-oxazolidine-2-thione (412 mg, 1.39 mmol) was suspended in dichloromethane (3.3 mL), and then cooled to 0° C. in an ice bath. Dimethylaminopyridine (16 mg, 0.131 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (315 mg, 1.64 mmol) were added in this order. A solution of a commercially available reagent of (E)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-enoic acid (476 mg, 1.27 mmol) in dichloromethane (3.4 mL) was then added. After stirring at 0° C. for 2 hours, an aqueous solution (50 mL) of 10% sodium dihydrogen phosphate and ethyl acetate (50 mL) were added and the mixture was separated. The organic layer was washed with a saturated aqueous solution (40 mL) of sodium chloride, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 445 mg (0.681 mmol, 54% yield) of (E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-one (ESI (LC/MS positive mode) m/z 654 (M+H); Rt 3.07 min.).

Provenance & Evidence