Reaction Steps
A small reaction tube fitted with screw cap containing a septa is charged with (4S,5S)-3-(4-chlorophenyl)-4-(3-hydroxyphenyl)-5-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)-methyl)oxazolidin-2-one (25 mg, 0.055 mmol) and DMF (0.5 mL). Potassium carbonate (25 mg, 0.18 mmol) and 2-iodopropane (18 μL, 0.18 mmol) are then added and the vessel is heated to 50° C. for 4 h, then cooled to room temperature. The reaction is quenched with water, and extracted with EtOAc, dried over MgSO4, filtered and concentrated. The title compound is then obtained after flash chromatography (12 g Redisep, 30-50% EtOAc/hexanes). 1H NMR (acetone-d6, 400 MHz) δ 9.22 (br, s 1H), 8.72 (br, s, 1H), 8.33 (ddd, J=8.0, 1.8, 1.8 Hz, 1H), 7.52 (dd, J=7.9, 4.8 Hz, 1H), 7.46-7.42 (m, 2H), 7.32 (t, J=7.6 Hz, 1H), 7.27-7.24 (m, 2H), 7.09 (app t, J=1.9 Hz, 1H), 7.04 (d, J=7.7 Hz, 1H), 6.86 (ddd, J=8.3, 2.5, 0.8 Hz, 1H), 5.72 (d, J=5.0 Hz, 1H), 5.51 (dd, J=14.7, 5.9 Hz, 1H), 5.44 (dd, J=14.7, 4.1 Hz, 1H), 5.12 (ddd, J=5.8, 5.0, 4.2 Hz, 1H), 4.60 (septet, J=6.0 Hz, 1H), 1.24 (d, J=6.0 Hz, 3H, 1.21 (d, J=6.0 Hz, 3H); HPLC-MS calculated C25H23ClN6O3 (M+H+) 491.2, found 491.2.
