2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid → tert-butyl N-(5-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzyl)-N-methylglycinate

Participants

Reaction Steps

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 60 (256.87 mg; 0.83 mmol) and Intermediate 36 (202.74 mg; 0.75 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1), affording the title compound as a pale yellow oil. 1H NMR (CDCl3) δ 8.42 (d, J=1.4 Hz, 1H), 8.26 (dd, J=7.0, 2.1 Hz, 1H), 8.18-8.09 (m, 2H), 7.41-7.34 (m, 3H), 7.29-7.23 (m, 1H), 7.19 (t, J=9.0 Hz, 1H), 7.12-7.10 (m, 1H), 4.27-4.17 (m, 2H), 3.90 (s, 2H), 3.38 (s, 3H), 3.28 (s, 2H), 2.47-2.29 (m, 5H), 1.51 (s, 9H), 1.05 (t, J=7.5 Hz, 3H). LC/MS (Method B): 546.3 (M+H)+. HPLC (Method A) Rt 5.04 min (Purity: 99.5%).

Provenance & Evidence