Benzyl Alcohol → HCID 178464366, compound

Participants

Reaction Steps

A solution of trans-{4-[({2-[({1-[3,5-bis(trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid (racemate compound (I), 20 g, 24.61 mmol) synthesized by the method described in Patent document 2 (International Patent Publication WO2008/129951), Example 45 in anhydrous dichloromethane (200 mL) was added with benzyl alcohol (2.93 g, 27.07 mmol), DMAP (300 mg, 2.46 mmol) and WSC.HCl (5.19 g, 27.07 mmol) under ice cooling, and the mixture was warmed to room temperature, and stirred for 16 hours. The reaction mixture was added with water (100 mL), and the mixture was extracted with chloroform (500 mL). The organic layer was washed with 2 M aqueous hydrochloric acid (100 mL) and saturated brine (100 mL), dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, and the resulting residue was purified by column chromatography (silica gel: 350 g, developing solvent: N-hexane/ethyl acetate=3/1→1/1) to obtain trans-{4-[({2-[({1-[3,5-bis(trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid benzyl ester (21.15 g, yield: 95.2%) as white amorphous.

Provenance & Evidence