(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)-propionic 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) (500 mg, 1.5 mmol), dichloromethane (14 mL) and propanoyloxymethyl carbonochloridate (7b) gave the titled product in 75% yield (520.9 mg, 1.10 mmol). 1H NMR (400 MHz, CDCl3): δ 7.48 (dd, 1H), 7.24 (t, 1H), 7.16 (dd, 1H), 5.74 (q, 2H), 5.28 (t, 1H), 3.12-3.18 (m, 4.83 (m, 1H), 4.05 (t, 1H), 3.79 (dd, 1H), 3.67 (ddd, 1H), 3.56 (dt, 1H), 3.12-3.18(m, 4H), 3.10 (dt, 1H), 2.32-2.46 (m, 4H), 2.17-2.20 (m, 2H), 1.12 (t, 3H). MS-APCI (m/z+): 473 (M+H).

Provenance & Evidence