Water → HCID 11226859, compound

Participants

Reaction Steps

Acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamic acid 1-chloro-ethyl ester (11) (0.20 g, 0.41 mmol), cesium cyclopentanecarboxylate (0.20 g, 0.81 mmol) and sodium iodide (0.061 g, 0.41 mmol) in acetonitrile (15 mL) were heated to reflux overnight. Upon cooling to RT, water was added and the reaction mixture was extracted with ethyl acetate and then with dichloromethane. The organic phases were washed with brine, combined, dried over magnesium sulfate, filtered, and conc in vacuo. The isolated residue was subjected to silica gel flash chromatography, eluting with MeOH/CH2Cl2 gradient (0-4% MeOH over 1 hour and 20 minutes) to afford the title compound. Isolated yield: 63%. 1H NMR (400 MHz, DMSO-d6): δ 7.39 (dd, 1H), 7.35-7.31 (m, 1H), 7.24-7.20 (m, 1H), 6.73-6.69 (m, 1H), 4.74-4.70 (m, 1H), 4.12-3.93 (m, 2H), 3.88-3.73 (m, 2H), 3.39-3.28 (m, 2H), 3.26 (s, 3H), 3.18-3.11 (m, 1H), 3.06-3.03 (m, 2H), 2.76-2.68 (m, 1H), 2.37 (d, 3H), 2.15-2.06 (m, 2H), 2.00-1.97-(m, 2H), 1.80-1.70 (m, 2H), 1.68-1.56 (m, 2H), 1.54-1.43 (m+dd, 4H).

Provenance & Evidence