Hydrochloric Acid → (2S,4S)-4-(3-carboxy-propionylamino)-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid

Participants

Reaction Steps

To a stirred solution of (2S,4S)-4-(3-carboxy-propionylamino)-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester (25 mg, 0.056 mmol) in 2 ml EtOH was added 1 ml of aqueous 1M NaOH and the solution was stirred for an hour. The reaction mixture was acidified to pH=2 to 3 with aqueous 1M HCl. Solvent was removed under reduced pressure and the residue was purified by RP-HPLC to give 14 mg (2S,4S)-4-(3-carboxy-propionylamino)-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid. MS m/z 418.2 (M+H), 416.2 (M−H). LC/MS (Condition A): 1.18 min 1H NMR (400 MHz, DMSO-d6): 0.98-1.00 (d, J=6.82 Hz, 3H), 1.39-1.45 (m, 1H), 1.71-1.78 (m, 1H), 2.18-2.38 (m, 5H), 2.67-2.76 (m, 2H), 3.97-4.07 (m, 1H), 7.26-7.28 (d, J=8.34 Hz, 2H), 7.38-7.41 (m, 1H), 7.45-7.49 (t, J=7.83 Hz, 1H), 7.60-7.64 (m, 3H), 7.70-7.71 (t, J=1.77 Hz, 1H), 7.75-7.77 (d, J=8.84 Hz, 1H), 12.08 (br s, 2H).

Provenance & Evidence