Water → tert-butyl ((1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Participants

Reaction Steps

2-(3-((4-(((tert-Butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid 9b (170 mg, 0.33 mmol) was added to a solution of methylamine in tetrahydrofuran (2 N, 5 mL), followed by addition of 2-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (104 mg, 0.91 mmol) and then the reaction solution was stirred for 3 h. 20 mL of water and 20 mL of ethyl acetate were added, and the reaction solution was layered, the water phase was extracted with ethyl acetate (20 mL×1). 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. The resulting residue was purified by thin layer chromatography with elution system C to obtain the title product tert-butyl ((1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 9c (50 mg, a white solid) in 28% yield.

Provenance & Evidence