1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (E)-11,11-difluoro-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-octadec-3-en-1-one

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, (E)-11,11-difluoro-octadec-3-enoic acid (No. 6893453; 502.7 mg, 1.58 mmol) obtained in step B-4 and a commercially available reagent (S)-4-isopropyl-5,5-diphenyl-oxazolidine-2-thione (469.5 mg, 1.58 mmol) were dissolved in dichloromethane (7.5 mL), and the solution was cooled to 0° C. While maintaining the temperature at 0° C., N,N-dimethyl-4-aminopyridine (4-DMAP; 19.3 mg, 0.158 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (WSCl; 393.4 mg, 2.05 mmol) were sequentially added, and the mixture was stirred at 0° C. for 2 minutes and at room temperature for 19 hours. An aqueous solution (9.0 mL) of 10% sodium dihydrogen phosphate and ethyl acetate were added to the reaction solution before extraction. The organic layer was sequentially washed with water and a saturated brine, and dried over anhydrous sodium sulfate. After the organic layer was filtered and the solvent was distilled off, the resulting residue was purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.6) to obtain (E)-11,11-difluoro-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-octadec-3-en-1-one (No. 5547308; 647.9 mg, 3 steps, 34% yield).

Provenance & Evidence