Reaction #155342

Reaction equation

3-{2-[5-Fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionic acid

m-chloroperbenzoic acid

sodium hydrogen sulfite

→

3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethanesulfonyl}propionic acid

Yield 91.0%

Solvents

dichloromethane

methanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe resulting reaction mixture
3. 3
   Temperaturecooled
4. 4
   Extractionfollowed by extraction with dichloromethane
5. 5
   WashThe thus-obtained organic layer was washed with water
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified
8. 8
   ConcentrationThe purified product was concentrated under reduced pressure
9. 9
   Othersubjected to recrystallization from ethyl acetate-n-hexane

Procedure

3-{2-[5-Fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionic acid (2.26 g, 4.92 mmol) was dissolved in a mixed solvent of dichloromethane (100 ml) and methanol (20 ml), m-chloroperbenzoic acid (mCPBA, purity: 70%, 2.55 g, 10.33 mmol) was added thereto, and the mixture was then stirred at room temperature for 1 hour. The resulting reaction mixture was ice-cooled. An aqueous saturated sodium hydrogen sulfite solution (50 ml) was added to the reaction mixture, followed by extraction with dichloromethane. The thus-obtained organic layer was washed with water and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=100:0→100:10). The purified product was concentrated under reduced pressure and subjected to recrystallization from ethyl acetate-n-hexane, giving a pale yellow powder of 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethanesulfonyl}propionic acid (2.2 g, yield: 91%).

Source