Hydrochloric Acid → (+/-)-3-{4-[2-Cyclohexyl-1-(4'-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-2-hydroxy-propionic acid

Participants

Reaction Steps

To a mixture of (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-3-methyl-benzoylamino}-2-methyl-propionic acid ethyl ester (0.0571 g, 0.0978 mmol) in THF (1.0 mL) is added LiOH (1N aqueous, 1.0 mL) and stirred at RT for 4 d. The reaction mixture is acidified with 1N HCl (1.0 mL) and extracted with EtOAc (3×10 mL). Combined organic extracts are dried over Na2SO4, filtered, and conc. to provide (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-2-hydroxy-propionic acid (0.0474 g, 87%) as a white foam. MS (ES): 554.3 [M−H]−.

Provenance & Evidence