Hydrochloric Acid → 5'-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylthio)pyrimidin-5-yl]-2'-fluoro-4'-methoxy-2-methylbiphenyl-4-carboxylic acid

Participants

Reaction Steps

Methyl 5′-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylthio)pyrimidin-5-yl]-2′-fluoro-4′-methoxy-2-methylbiphenyl-4-carboxylate (43.8 mg, 0.061 mmol) was dissolved in 1,4-dioxane (1.86 mL) and water (1.16 mL). To the above stirred solution was added lithium hydroxide monohydrate (12.70 mg, 0.303 mmol). The resulting mixture was stirred at room temperature overnight. The reaction crude was then acidified with HCl (1N, aq) to give a milky mixture. This white mixture was dissolved into a clear solution by adding MeCN. The clear solution was purified by preparative HPLC (Kromasil 100-5C18, 100×21.1 mm) eluting with MeCN/water+0.1% TFA (10% to 100% organic in 10 min, hold 100% for 2 min, 20 mL/min). Related fractions were pooled and evaporated in vacuo to afford an aqueous mixture. The resulting aqueous mixture was extracted with EtOAc, washed with aqueous NaHCO3, dried (Na2SO4), filtered and concentrated to afford a light tan glass as the titled compound. LCMS calc.=709.15; found=710.06 (M+H)4. 1H NMR (500 MHz, CD3OD): δ 8.38 (s, 1H), 7.99 (s, 1H), 7.91 (s, 3H), 7.85 (d, J=8 Hz, 1H), 7.31 (d, J=8 Hz, 1H), 7.22 (d, J=8 Hz, 1H), 7.06 (d, J=11.5 Hz, 1H), 5.85 (br s, 1H), 4.75 (br d, J=17 Hz, 1H), 4.35 (t, J=7.25 Hz, 1H), 4.18 (br s, 1H), 3.90 (s, 3H), 2.60 (s, 3H), 2.26 (s, 3H), 0.69 (br d, J=5.5 Hz, 3H).

Provenance & Evidence