(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)-isobutyric acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl ester

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Reaction Steps

Following general procedure C, (S)-5-aminomethyl-3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-oxazolidin-2-one (2) (344.1 mg, 1.00 mmol), dichloromethane (9 mL) and isobutyroyloxymethyl carbonochloridate (7c) gave the titled product in 91% yield (446.3 mg, 0.92 mmol). 1H NMR (400 MHz, CDCl3): δ 7.48 (dd, 1H), 7.23 (t, 1H), 7.16 (dd, 1H), 5.73 (q, 2H), 5.28 (t, 1H), 4.80 (sept, 1H), 4.05 (t, 1H), 3.79 (dd, 1H), 3.67 (ddd, 1H), 3.57 (dt, 1H), 3.12-3.19 (m, 4H), 3.09 (dt, 1H), 2.55 (sept, 1H), 2.34-2.46 (m, 2H), 2.15-2.22 (m, 2H), 1.14 (dd, 6H). MS-APCI (m/z+): 487 (M+H).

Provenance & Evidence