Hydrochloric Acid → HCID 11961321, compound

Participants

Reaction Steps

10% NaOH (aq) (1 mL) was added to a solution of (S)-ethyl 3-(4-[3-(4-chloro-2-methylphenyl)benzyloxy]phenyl)-3-(1-methyl-1H-imidazol-2-yl)propanoate (9.10) (49 mg, 0.1 mmol) in EtOH (2 mL). The reaction mixture was stirred at room temperature for 4 hours. 1N HCl was added to neutralize the mixture to pH 6-7. The mixture was extracted with EtOAc (2×20 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was flash chromatographed (silica gel, 0-10% MeOH in DCM) to afford (S)-3-[4-(4′-chloro-2′-methyl-biphenyl-3-ylmethoxy)-phenyl]-3-(1-methyl-1H-imidazol-2-yl)-propionic acid (9) as a colorless oil. MS ESI (neg.) m/e: 459 (M−H). 1H NMR (500 MHz) (DMSO) δ 7.87 (broad s, 1H); 6.63-7.46 (m, 13H); 5.06 (s, 2H); 4.49 (dd, J=8.4, 3.2 Hz, 1H); 3.39 (s, 3H); 3.29 (dd, J=15.0, 8.5 Hz, 1H); 3.10 (dd, J=15.2, 3.0 Hz, 1H); 2.23 (s, 3H).

Provenance & Evidence