Hydrochloric Acid → 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid

Participants

Reaction Steps

Ethyl 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetate 9a (170 mg, 0.31 mmol) and lithium hydroxide (71 mg, 3.0 mmol) were added to 20 mL of a mixed solvent of tetrahydrofuran and water (V/V=1:1) and then the reaction solution was stirred for 3 h. 1M of hydrochloric acid was added dropwise until the pH of the reaction solution was 5, and then it was extracted with ethyl acetate (30 mL×2). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the title product 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid 9b (160 mg, a yellow oil), which was used directly in the next step.

Provenance & Evidence