Trifluoroacetic acid → HCID 9911411, compound

Participants

Reaction Steps

[[2-Ethyl-1-(2-bromo-phenylmethyl)-3-ureido-1H-indol-4-yl]oxy]acetic acid tert-butyl ester (0.7 g) was dissolved in 5 mL of dichloromethane and 1 mL of trifluoroacetic acid was added. After stirring for 4 hours the reaction mixture was concentrated to dryness, the residue dissolved in ethyl acetate and extracted with 1 N sodium hydroxide. This solution was acidified and extracted with ethyl acetate, the solvent removed by flash evaporation, and the residue slurried in 1 N hydrochloric acid. The resulting greenish solid was isolated by filtration and vacuum dried. This material was flash chromatographed on silica eluting with 19:1 ethyl acetate/methanol containing 2.5% acetic acid to provide [[2-ethyl-1-(2-bromo-phenylmethyl)-3-ureido-1H-indol-4-yl]oxy]acetic acid.

Provenance & Evidence