(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 → (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

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Reaction Steps

A solution of (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, 0.114 mmol) in THF (3 mL), methanol (3 mL) and 2 N aq. LiOH (1 mL) is stirred at rt for 2 h. The solvent is evaporated and the residue is dissolved in 2 N aq. HCl (10 mL) and extracted four times with DCM (4×20 mL). The org. extracts are combined, dried over MgSO4, filtered and concetrated. The crude product is purified by prep. HPLC to give the title compound (31 mg) as a white solid; LC-MS*: tR=0.86 min, [M+H]+=511.19; 1H NMR (CD3OD): δ 7.88 (s, 1H), 7.86 (s, 1H), 7.54 (s, 1H), 7.30 (s, 1H), 4.30-4.36 (m, 1H), 4.01 (s, 3H), 3.87-3.98 (m, 2H), 3.63 (s, 2H), 3.46 (dd, J1=12.5 Hz, J2=2.9 Hz, 1H), 3.24-3.32 (m, 2H), 2.81 (q, J=7.6 Hz, 2H), 2.42 (s, 3H), 2.07-2.17 (m, 2H), 1.86-1.98 (m, 4H), 1.74-1.82 (m, 2H), 1.32 (t, J=7.6 Hz, 3H).

Provenance & Evidence