2-Methylbenzenesulfonamide → HCID 18971765, compound

Participants

Reaction Steps

To a solution of acid 4'-methoxy-3'-(1-methyl-4-phenylbutoxy)-(±)[1,1'-biphenyl]-4-carboxylic acid, (0.257 g, 0.658 mmoles) in 10 ml of anhydrous methylene chloride under hydrogen atmosphere was added dimethylamino pyridine (88.46 mg, 0.728 mmoles); o-Toluenesulfonamide (0.122 g, 0.712 mmoles) and dicyclohexylcarbodiimide (0.124 g, 0.6 mmoles) the reaction mixture allowed to stir for 50 hours. The solvent was evaporated and the resulting solid triturated with methylene chloride:ether (~1:1) which lead to precipitation of by-product DCU which was filtered. Concentration of the mother liquor followed by 3 g additional triturations with ethyl acetate/ether (~1:1) caused additional deposit of white solid which was filtered. The clear filtrate was concentrated and purified on a silica gel column using methylene chloride/methanol as eluant (95:5). Concentration of fractions containing desired products gave a total of 0.37 g of white foamy solid. Recrystallization from ethyl acetate/hexane gave 0.208 grams of white solid. M.P.: 97°-100° C.

Provenance & Evidence