4-Isopropoxy-3-(methoxymethyl)benzoic acid → tert-butyl N-(3-{5-[4-isopropoxy-3-(methoxymethyl)phenyl]-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 56 (201.83 mg; 0.90 mmol) and Intermediate 51 (220 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 solid. 1H NMR (CDCl3) δ 8.25 (d, J=2.2 Hz, 1H), 8.12 (d, J=1.7 Hz, 1H), 8.09 (d, J=2.2 Hz, 1H), 8.06 (br s, 1H), 7.57-7.55 (m, 1H), 7.47 (t, J=7.5 Hz, 1H), 6.98 (d, J=8.9 Hz, 1H), 4.70 (quint., J=6.1 Hz, 1H), 4.54 (s, 2H), 3.78 (s, 2H), 3.50 (s, 3H), 3.23 (s, 2H), 2.41 (s, 3H), 1.50 (s, 9H), 1.40 (d, J=6.0 Hz, 6H). HPLC (Method A) Rt 4.96 min (Purity: 100.0%).

Provenance & Evidence