Acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin 5(R)-ylmethyl}-carbamic acid 1(R,S)-chloro-ethyl ester (11) (0.49 g, 1 mmol), mercury(II) acetate (0.37 g, 1.175 mmol), and acetic acid (6.3 mL, 109 mmol) are stirred at RT overnight. Ether and water are added and the layers are separated. The organic layer is washed several times with water, brine, dried over Na2SO4 and conc in vacuo. After purification by silica gel chromatography, the product is re-dissolved in CH2Cl2 and washed with several portions of sat NaHCO3, water, dried over Na2SO4 and conc in vacuo to give the title compound in 43% yield (0.51 g) as a mixture of two diastereomers in a 1:1 ratio. 1H NMR (400 MHz, CDCl3): δ 7.46 (dt, 1H), 7.21 (m, 1H), 7.13 (m, 1H), 6.88 (q, 1H), 4.82 (m, 0.5H), 4.75 (m, 0.5H), 4.13 (m, 1H), 4.04 (m, 2H), 3.73 (dd, 0.5H), 3.67 (dd, 0.5H), 3.12 (m, 5H), 2.55 (s, 1.5H), 2.53 (s, 1.5H), 2.38 (m, 2H), 2.17 (m, 2H), 2.13 (s, 1.5H), 2.06 (s, 1.5H), 1.57 (d, 1.5H), 1.54 (d, 1.5H). MS-APCI (m/z+): 341, 385, 427, 515.
