2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → Methyl 2-chloro-5-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

Participants

Reaction Steps

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 28 (461.34 mg; 1.80 mmol) and Intermediate 54 (342.95 mg; 1.50 mmol). The reaction mixture was filtered through a SPE NH2 column (10 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (10 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, 300 MHz) δ 8.68 (d, J=2.1 Hz, 1H), 8.43 (d, J=1.1 Hz, 1H), 8.25 (dd, J=8.3, 2.1 Hz, 1H), 8.17 (dd, J=7.9, 1.7 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.36-7.24 (m, 4H), 7.13 (d, J=7.2 Hz, 1H), 4.28-4.19 (m, 2H), 4 (s, 3H), 3.34 (s, 3H), 2.08 (s, 3H). LC/MS (Method B): 449.1 (M+H)+. HPLC (Method A) Rt 6.10 min (Purity: 96.0%).

Provenance & Evidence