2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → tert-butyl N-(2-fluoro-5-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-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 28 (192.22 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 slightly yellow oil. 1H NMR (CDCl3) δ 8.42 (d, J=1.4 Hz, 1H), 8.27 (d, J=5.8 Hz, 1H), 8.19-8.09 (m, 2H), 7.36-7.12 (m, 6H), 4.23 (s, 2H), 3.92 (s, 2H), 3.33 (s, 3H), 3.29 (s, 2H), 2.48 (s, 3H), 2.08 (s, 3H), 1.51 (s, 9H). LC/MS (Method B): 532.3 (M+H)+. HPLC (Method A) Rt 4.85 min (Purity: 98.6%).

Provenance & Evidence