2-Benzoyl-4-bromobenzoic acid → 2-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide

Participants

Reaction Steps

[Step 1] To a solution (20 ml) of 2-benzoyl-4-bromobenzoic acid (2.0 g) in THF were added 1-(4-methanesulfonylbenzylamino)pentan-2-ol (1.8 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.9 g), 1-hydroxy-1H-benzotriazole monohydrate (1.0 g), acetonitrile (20 ml) and triethylamine (5 ml) at room temperature. The reaction mixture was stirred at room temperature for 12 hrs. and concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 1N-hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crystals were washed with diisopropyl ether to give 2-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide (3.0 g).

Provenance & Evidence