Tetrahydrofuran → HCID 25181716, compound

Participants

Reaction Steps

To 7-chloro-3-[4-(2-hydroxy-ethylsulfanyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (100 mg) in a mixture of THF and MeOH (1:5, 12 mL) was added a solution of OXONE™ (294 mg) in water (3 mL) at 0° C. The reaction mixture was stirred for 1.5 h, and NaHCO3 (sat aq, 20 mL) added. The resulting mixture was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give a yellow-brown oil. The crude residue was purified by flash chromatography (EtOAc/hexane) to give 7-chloro-3-[4-(2-hydroxyethane-sulfonyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (23.6 mg) as an off-white powder. MS=512 [M+H]+; MP=172.2-173.5° C.

Provenance & Evidence