Hydrochloric Acid → HCID 25010059, compound

Participants

Reaction Steps

To a solution of methyl 4′-methoxy-2-methyl-2″-{[(4S,5R)-4-methyl-5-(2-methylpyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]methyl}-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (30.1 mg, 0.050 mmol) in 1,4-dioxane (1.5 mL) and water (1.5 mL) was added 1M aqueous LiOH (0.498 mL, 0.498 mmol). The mixture was stirred at room temperature for 4 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 crude material was purified by preparative HPLC reverse phase (C-18), eluting with MeCN/water. The fractions were collected and lyophilized to give 4′-methoxy-2-methyl-2″-{[(4S,5R)-4-methyl-5-(2-methylpyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]methyl}-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylic acid. LCMS calc.=591.2; found=591.1 (M+1)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers) δ 8.83 (s, 1H); 8.02 (s, 1H); 7.94 (t, J=10.0 Hz, 1H); 7.72 (s, 0.5H); 7.69 (t, J=6.0 Hz, 1H); 7.64 (s, 0.5H); 7.49-7.43 (m, 3H); 7.40 (d, J=5.2 Hz, 0.5H); 7.35 (d, J=5.4 Hz, 0.5H); 7.31 (m, 1H); 7.16 (dd, J=2.1, 6.0 Hz, 1H); 7.12 (t, J=8.8 Hz, 1H); 5.56 (d, J=8.1 Hz, 0.5H); 5.26 (d, J=8.2 Hz, 0.5H); 4.94 (dd, J=8.7, 15.7 Hz, 1H); 4.77 (br s, 1H); 4.20 (d, J=15.8 Hz, 0.5H); 4.00 (d, J=15.7 Hz, 0.5H); 3.90 (s, 1.5H); 3.89 (s, 1.5H); 3.89-3.81 (m, 1H); 2.82 (s, 1.5H); 2.81 (s, 1.5H); 2.41 (s, 1.5H); 2.36 (s, 1.5H); 0.62 (d, J=6.5 Hz, 1.5H); 0.49 (d, J=6.5 Hz, 1.5H).

Provenance & Evidence