Hydrochloric Acid → HCID 24800871, compound

Participants

Reaction Steps

Methyl 6-(2-(3-(4′-(thiomorpholinomethyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate (105 mg, 0.199 mmol) was dissolved in THF/H2O (3:2, 15 mL) and LiOH (14 mg, 0.60 mmol) was added. The reaction solution was stirred at room temperature under an atmosphere of Ar for 40 min before the addition of aqueous 1 N HCl to pH 4. The reaction solution was diluted with CH2Cl2 and the organic and aqueous layers were separated. The aqueous layer was made basic to pH 8 with the addition of saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic phases were combined, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by tritration in ether to provide 6-(2-(3-(4′-(thiomorpholinomethyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylic acid (89 mg, 87%): 1H NMR (CDCl3, 600 MHz) δ 8.21 (d, 1H, J=6.9 Hz), 8.05-8.00 (m, 3H), 7.52 (d, 2H, J=8.1 Hz), 7.49 (d, 2H, J=8.1 Hz), 7.40 (d, 2H, J=8.0 Hz), 7.32 (d, 2H, J=8.0 Hz), 3.83 (s, 2H), 3.50 (t, 2H, J=7.5 Hz), 3.15 (t, 2H, J=7.5 Hz), 2.99 (s, 4H), 2.83-2.82 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 187.3, 157.4, 152.2, 149.6, 145.5, 140.7, 139.6, 138.9, 138.6, 130.4, 128.9, 128.0, 127.2, 127.1, 124.5, 123.2, 62.4, 54.2, 40.6, 29.3, 26.9; HR ESI-TOF m/z 514.1784 (M+H+, C29H27N3O4S, requires 514.1795).

Provenance & Evidence