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-methyl-beta-alaninate

Participants

Reaction Steps

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 63 (268.44 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 colorless oil. 1H NMR (CDCl3) δ 8.42 (d, J=1.4 Hz, 1H), 8.25-8.22 (m, 1H), 8.17 (dd, J=7.8, 1.9 Hz, 1H), 8.12-8.07 (m, 1H), 7.36-7.23 (m, 4H), 7.20-7.12 (m, 2H), 4.23 (s, 2H), 3.65 (s, 2H), 3.33 (s, 3H), 2.80 (t, J=7.3 Hz, 2H), 2.49 (t, J=7.2 Hz, 2H), 2.27 (s, 3H), 2.08 (s, 3H), 1.45 (s, 9H). 19F NMR (CDCl3) δ-113.6 ppm. LC/MS (Method B): 546.4 (M+H)+. HPLC (Method A) Rt 5 min (Purity: 97.8%).

Provenance & Evidence