Hydrochloric Acid → HCID 178461717, compound

Participants

Reaction Steps

Next, to a solution of (2R,4S)-5-(3′-chloro-biphenyl-4-yl)-4-[(3-hydroxy-isoxazole-5-carbonyl)-amino]-2-methyl-pentanoic acid ethyl ester (73 mg, 0.16 mmol) in ethanol (4 mL) is added 1N NaOH (2 mL) and the resulting mixture is stirred at room temperature for 2 hours. The mixture is acidified with 1N HCl and the solvent is removed under reduced pressure. The resulting residue is purified by preparative HPLC using a gradient of 10% MeCN/water to 100% MeCN (0.1% TFA) to give (2R,4S)-5-(3′-chloro-biphenyl-4-yl)-4-[(3-hydroxy-isoxazole-5-carbonyl)-amino]-2-methyl-pentanoic acid; HPLC Retention time 1.05 minutes (condition C): MS 429.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07 (d, 3H) 1.58 (ddd, J=13.89, 9.98, 4.42 Hz, 1H) 1.87 (ddd, J=13.71, 9.66, 3.92 Hz, 1H) 2.41 (ddd, J=9.54, 7.14, 4.55 Hz, 1H) 2.82 (dd, J=6.69, 3.41 Hz, 2H) 4.10-4.24 (m, 1H) 6.50 (s, 1H) 7.28 (d, J=8.34 Hz, 2H) 7.36-7.42 (m, 1H) 7.47 (t, J=7.83 Hz, 1H) 7.58-7.65 (m, 3H) 7.70 (t, J=1.89 Hz, 1H) 8.66 (d, J=8.59 Hz, 1H).

Provenance & Evidence