HCID 46206527, compound → HCID 46206856, compound

Participants

Reaction Steps

A solution of [6-methyl-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid (example 2-28) (70 mg, 0.183 mmol) in methanol (8 mL) was hydrogenated using a H-cube hydrogenation reactor with a flow rate of 1 mL/min and a 10% palladium on carbon catalyst cartridge at 30° C. under 10 bar hydrogen pressure. After the reaction was complete (monitored by TLC, 4% methanol in dichloromethane), the solvent was evaporated in vacuo. Reverse-phase preparative HPLC (using a Waters® Delta-Prep™ 3000 with a Varian Pursuit® C-18 column [10 μm, 20×150 mm]) gave [4-(4-methanesulfonyl-benzyl)-6-methyl-naphthalen-2-yl]-acetic acid (14.4 mg, 21%) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm: 7.83 (d, J=8.4 Hz, 2 H), 7.74 (d, J=8.7 Hz, 1 H), 7.66 (s, 1H), 7.60 (s, 1 H), 7.38 (d, J=8.4 Hz, 2 H), 7.32 (d, J=8.7 Hz, 1 H), 7.22 (s, 1 H), 4.48 (s, 2 H), 3.78 (s, 2 H), 3.02 (s, 3 H), 2.46 (s, 3 H); HRMS cald. for O21H20O4S (ESI+) [(M+Na)+] 391.0974, obsd. 391.0976.

Provenance & Evidence