Ammonium Chloride → 1-(4-bromo-5-fluoro-2-hydroxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide

Participants

Reaction Steps

A solution of N-(4-methoxybenzyl)isoxazol-3-amine (3.37 g, 16.49 mmol) in THF (30.0 ml) was cooled to −78° C. LHMDS (15.74 ml, 15.74 mmol) was then added dropwise and the acetone/dryice bath was removed for 5 minutes. The solution was then returned to −78° C. and a solution of perfluorophenyl 1-(4-bromo-5-fluoro-2-hydroxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (4.35 g, 7.50 mmol) in THF (30.0 ml) was added dropwise. The resulting solution was stirred for 4 hours warming to room temperature. Saturated ammonium chloride was added to the reaction mixture. The resulting mixture was transferred to a sep. funnel containing water and the aqueous layer was washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to an oil. The crude product was purified by ISCO MPLC (100% heptanes to 60% 3:1 EtOAc:EtOH). The product eluted at 50% 3:1 EtOAc:EtOH. m/z (ESI) 602.1 (M+1)±.

Provenance & Evidence