Potassium Hydroxide → 6-Chloro-2-fluoro-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzoic acid

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Reaction Steps

A 100 mL, round-bottomed flask was charged with benzyl 6-chloro-2-fluoro-3-(3-(4-methoxyphenoxy)-N-(3-(4-methoxyphenoxy)propylsulfonyl)propylsulfonamido)benzoate (1.08 g, 1.47 mmol), potassium hydroxide (4.40 mL, 4.40 mmol) and MeOH (10 mL). The reaction mixture was stirred at room temperature until TLC showed that the starting material had been consumed (about 12 hours). HCl (5 mL, 1N) was added. Then the reaction mixture was partitioned between EtOAc (500 mL) and water (100 mL). The phases were separated, and the aqueous phase was extracted with EtOAc (3×200 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield crude 6-chloro-2-fluoro-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzoic acid. The crude product was purified by silica gel chromatography (EtOAc/hexane from 1/4 to 1/0, v/v) to afford 6-chloro-2-fluoro-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzoic acid (0.58 g, 95.1%). 1H NMR (400 MHz, CDCl3) δ 10.02 (s, 1H), 7.39-7.53 (m, 2H), 6.81 (m, 4H), 4.01 (t, 2H), 3.64 (s, 3H), 3.34 (t, 2H), 2.11 (m, 2H).

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