Hydrochloric Acid → 4-{4-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl]-5-ethyl-1,3-thiazol-2-yl}-3-methylbenzoic acid

Participants

Reaction Steps

To a solution of methyl 4-{4-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl]-5-ethyl-1,3-thiazol-2-yl}-3-methylbenzoate (11 mg, 0.015 mmol) in 1,4-dioxane (0.4 mL) and water (0.4 mL), was added 1N LiOH (0.151 mL, 0.151 mmol). The mixture was stirred at room temperature for 2 h. The mixture was acidified with 1N HCl. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The residue was purified by preparative HPLC reverse phase (C-18), eluting with MeCN/water containing 0.1% TFA. The fractions were collected and lyophilized to give 4-{4-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl]-5-ethyl-1,3-thiazol-2-yl}-3-methylbenzoic acid. LCMS calc.=717.1; found=717.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 8.05 (s, 1H); 7.99 (d, J=8.1 Hz, 1H); 7.89 (d, J=8.1 Hz, 1H); 7.87 (s, 1H); 7.78 (s, 1H); 7.74 (d, J=8.0 Hz, 1H); 7.71 (s, 2H); 7.57 (d, J=7.9 Hz, 1H); 5.61 (d, J=8.0 Hz, 1H); 4.94 (d, J=15.7 Hz, 1H); 4.25 (d, J=15.7 Hz, 1H); 4.04-3.98 (m, 1H); 2.89-2.76 (m, 2H); 2.69 (s, 3H); 1.37 (t, J=7.5 Hz, 3H); 0.60 (d, J=6.5 Hz, 3H).

Provenance & Evidence