Potassium Carbonate → HCID 25181715, compound

Participants

Reaction Conditions

Reaction Steps

K2CO3 (12 mg) was added the mixture of N-(5-chloro-2-{3-[4-(2,3-dihydroxy-propylsulfamoyl)-phenyl]-propionyl}-phenyl)-N-phenyl-oxalamic acid methyl ester and N-(5-chloro-2-{3-[4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethylsulfamoyl)-phenyl]-propionyl}-phenyl)-N-phenyl-oxalamic acid methyl ester (0.05 mmol) in MeOH (5 mL), and the resulting mixture stirred at 80° C. for 1.5 h. The reaction mixture was then cooled and evaporated under reduced pressure. The residue was partitioned between water and EtOAc, the organic layer separated, and the aqueous layer extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified twice by preparative TLC (DCM/MeOH, 9:1) and then (DCM/MeOH, 95:5) to provide 7-chloro-3-[4-(2,3-dihydroxy-propylsulfamoyl)-benzyl]-4-oxo-1-phenyl-1,4-di-hydroquinoline-2-carboxylic acid methyl ester as light brown powder. MS=556.8 [M+H]+ and 554.9 [M−H]−.

Provenance & Evidence