HCID 46189870, compound → HCID 46205532, compound

Participants

Reaction Steps

A solution of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-3-methyl-naphthalen-2-yl]-acetic acid (60 mg, 0.15 mmol) (example 6-1) in methanol (12 mL) was hydrogenated using a H-cube hydrogenation reactor with a flow rate of 1.7 mL/min and a 10% palladium on carbon catalyst cartridge at 20° C. under 10 bar hydrogen pressure. The reaction mixture was concentrated in vacuo. The crude product was purified using flash chromatography (RediSep® Flash column, 230-400 mesh, 2%-5% methanol in dichloromethane) to give 11 mg (18%) of {6-fluoro-4-[hydroxy-(4-methanesulfonyl-phenyl)-methyl]-3-methyl-naphthalen-2-yl}-acetic acid as an oil. 1H NMR (300 MHz, CDCl3) δ ppm: 7.82 (d, J=8.2 Hz, 2 H), 7.74 (dd, J=9.1, 6.0 Hz, 1 H), 7.61-7.70 (m, 2 H), 7.49 (d, J=8.2 Hz, 2 H), 7.15 (td, J=8.3, 2.1 Hz, 1 H), 6.73 (s, 1 H), 3.86 (br. s, 1 H), 3.48 (s, 2 H), 3.01 (s, 3 H), 2.41 (br. s, 3 H); HRMS (ESI+) cald. for C21H19FO5S [(M+Na)] 425.0829, obsd. 425.0827.

Provenance & Evidence