Hydrochloric Acid → (S)-2-((3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)amino)acetic acid ethyl ester

Participants

Reaction Steps

A solution of (S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole (500 mg, 1.15 mmol), glycine ethylester hydrochloride (320 mg, 2.30 mmol), of which the hydrochloride was removed by filtration over a carbonate loaded silica resin prior to use, and DIPEA (0.2 mL) in methanol (3 mL) is stirred at 60° C. for 3 days. The mixture is diluted with DCM and washed with sat. aq. NaHCO3 solution. The aq. phase is extracted once with DCM. The combined org. extracts are dried over Na2SO4, filtered and concentrated. The crude product is purified by prep. TLC using DCM:methanol 9:1 to give (S)-2-((3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)amino)acetic acid ethyl ester (60 mg) as a white solid; LC-MS: tR=1.03 min, [M+H]+=537.29.

Provenance & Evidence