HCID 59350853, compound → HCID 59350814, compound

Participants

Reaction Steps

A solution of [6-fluoro-4-(4-methylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid methyl ester (prepared in an analogous manner to example 2-1) in methanol (20 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. The reaction gave a mixture of alcohol {6-fluoro-4-[hydroxy-(4-methylsulfamoyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester and the corresponding fully hydrogenated product [6-fluoro-4-(4-methylsulfamoyl-benzyl)-naphthalen-2-yl]acetic acid methyl ester. Reverse-phase preparative HPLC (using a Waters® Delta-Prep™ 3000 with a Varian Pursuit® C-18 column [10 μm, 20×150 mm]) was used to separate these products, giving {6-fluoro-4-[hydroxy-(4-methylsulfamoyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester (4.0 mg) as 3.0 mg of a white solid. MS cald. for C21H20FNO5S [(M−H)−] 417, obsd. 416.

Provenance & Evidence