Hydrochloric Acid → HCID 24969101, compound

Participants

Reaction Steps

Methyl 3′-[3-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyrazin-2-yl]-4′-fluoro-2-methylbiphenyl-4-carboxylate (Step F, 16 mg, 0.025 mmol) and lithium hydroxide monohydrate (5.18 mg, 0.124 mmol) were stirred in 1,4-dioxane (0.914 mL)/water (0.571 mL) at room temperature for 2 days. Crude mixture was acidified with HCl (1N) and 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% in 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 water and then with brine, dried (Na2SO4), filtered and concentrated to afford a colorless glass as the titled compound. LCMS calc. 633.15=; found=634.25 (M+H)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers): δ 8.70 (d, J=2.5 Hz, 1H), 8.68 (d, J=2.5 Hz, 1H), 8.01 (s, 1H), 7.95 (dd, J=8, 1.5 Hz, 1H), 7.89 (s, 1H), 7.78 (s, 1H), 7.51-7.46 (m, 2H), 7.37 (d, J=8 Hz, 1H), 7.31 (t, J=8 Hz, 1H), 5.74 (d, J=8.5 Hz, 1H), 4.95 (d, J=17 Hz, 1H), 4.44-4.36 (m, 2H), 2.37 (s, 3H), 0.77 (d, J=6 Hz, 3H).

Provenance & Evidence