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

Participants

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) (589.0 mg, 1.72 mmol) in dichloromethane (14 mL) and 3,3-dimethyl-butyroxymethyl carbonochloridate (7 g) gave the titled product in 46% yield (407.2 mg, 0.79 mmol). 1H NMR (400 MHz, CDCl3): δ 7.48 (dd, 1H), 7.24 (t, 1H), 7.16 (dd, 1H), 5.73 (q, 2H), 5.26 (t, 1H), 4.75-4.82 (m, 1H), 4.05 (t, 1H), 3.78 (dd, 1H), 3.68 (ddd, 1H), 3.56 (dt, 1H), 3.13-3.19 (m, 4H), 3.10 (dt, 1H), 2.35-2.46 (m, 2H), 2.16-2.25(m, 4H), 1.00 (s, 9H).

Provenance & Evidence