(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)-benzoic 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) (500.0 mg, 1.5 mmol) in dichloromethane (14 mL) and benzoyloxymethyl carbonochloridate (7k) gave the titled product in 98% yield (744.5 mg, 1.43 mmol). 1H NMR (400 MHz, CDCl3): δ 8.05 (d, 2H), 7.60 (t, 1H), 7.46 (q, 3H), 7.20 (t, 1H), 7.13 (dd, 1H), 5.98 (q, 2H), 5.36 (t, 1H), 4.77-4.83 (m, 1H), 4.05 (t, 1H), 3.80 (dd, 1H), 3.68 (ddd, 1H), 3.57 (dt, 1H), 3.12-3.19 (m, 4H), 3.08 (dt, 1H), 2.31-2.45 (m, 2H), 2.13-2.21 (m, 2H).

Provenance & Evidence