Hydrochloric Acid → HCID 11856120, compound

Participants

Reaction Steps

Lithium hydroxide monohydrate (138 mg, 3.3 mmol) was added in one portion to a stirred solution of [3-(1-benzenesulfonyl-1H-pyrrol-2-ylmethyl)-5-fluoro-2-methyl-indol-1-yl]-acetic acid ethyl ester (507 mg, 1.1 mmol) in tetrahydrofuran:water (2:1; 10 ml) and the resulting mixture stirred at room temperature for 3 h. The solution was adjusted to pH 1 with 1M hydrochloric acid and then concentrated in vacuo to leave a yellow solid. The solid was partitioned between ethyl acetate (30 ml) and water (30 ml) and then the organic layer separated. The aqueous layer was extracted with ethyl acetate (2×20 ml) and the combined organic extracts were then dried and concentrated in vacuo to leave an off-white solid. Purification by flash column chromatography on silica gel eluting with 10% methanol:dichloromethane gave the carboxylic acid (130 mg, 28%) as a white solid, δH (250 MHz, d6-DMSO) 7.84 (2H, d J 7.1 Hz, Ar), 7.74 (1H, d J 7.1 Hz, Ar), 7.65-7.59 (2H, m, Ar), 7.44-7.41 (1H, m, Ar), 7.35-7.30 (1H, m, Ar), 6.82 (1H, td J 9.3, 2.4 Hz, Ar), 6.42 (1H, dd J 9.8, 2.4 Hz, Pyrrole-CH), 6.23-6.21 (1H, m, Pyrrole-CH), 5.56 (1H, br s, Pyrrole-CH), 4.94 (2H, s, CH2-Pyrrole), 4.02 (2H, s, CH2CO2H), 2.52 (3H, masked s, CCH3); Tr=1.63, m/z (ES+) (M+H)+ 427.19.

Provenance & Evidence