(R)-propionic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester → (S)-3-methyl-butyric acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl ester

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Following general procedure C, (S)-5-aminomethyl-3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-oxazolidin-2-one (2) (760.0 mg, 2.2 mmol) in dichloromethane (21 mL) and 3-methyl-butyroxymethyl carbonochloridate (7d) gave the titled product in 93% yield (1030.0 mg, 2.06 mmol). 1H NMR (400 MHz, CDCl3): δ 7.47 (dd, 1H), 7.23 (t, 1H), 7.16 (dd, 1H), 5.73 (q, 2H), 5.37 (t, 1H) 4.76-4.82 (m, 1H), 4.05 (t, 1H), 3.78 (dd, 1H), 3.67 (ddd, 1H), 3.55 (dt, 1H), 3.12-3.19 (m, 4H), 3.09 (dt, 1H), 2.34-2.45 (m, 2H), 2.14-2.21 (m, 2H), 2.07 (sept, 1H), 0.92 (dd, 6H). MS-APCI (m/z+): 501 (M+H).

Provenance & Evidence