1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[5-({(2S)-3-[benzyl(4-{4-[(4-benzylpiperidin-1-yl)carbonyl]phenyl}-cyclohexyl)amino]-2-hydroxypropyl}oxy)-2-(benzyloxy)phenyl]methanesulfonamide

Participants

Reaction Steps

A solution of 2 g (2.88 mmol) of trans-4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}benzoic acid (Preparation 1), 0.78 g (5.76 mmol) of 1-hydroxybenzotriazole, 1.1 g (5.76 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1.2 ml of triethylamine and 1.01 ml (5.76 mmol) of 4-benzylpiperidine in a mixture of 26 ml of dichloromethane and 5 ml of acetonitrile is stirred for 24 hours. The solvents are evaporated under reduced pressure. Dichloromethane and water are added and the organic phase is washed three times with water. The organic phases are dried over magnesium sulfate and concentrated under reduced pressure. N-[5-({(2S)-3-[benzyl(4-{4-[(4-benzylpiperidin-1-yl)carbonyl]phenyl}-cyclohexyl)amino]-2-hydroxypropyl}oxy)-2-(benzyloxy)phenyl]methanesulfonamide is obtained in the form of a white solid (1.355 g, 57%) after purification on silica gel (eluent: dichloromethane/methanol 90/10). [M+H+]=816.6.

Provenance & Evidence