Hydrochloric Acid → HCID 178453557, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-(tert-butoxycarbonyl((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)amino)propanoate (485 mg, 0.94 mmol) in EtOH (10 mL) was added aqueous NaOH (2 mL, 20%, 5.0 equiv) and refluxed for 2 h. Then the reaction was cooled to 0° C., the pH of the solution was adjusted to 6 using 1M HCl, concentrated and the residue was dissolved in DCM, washed with water, dried and concentrated to give 3-(tert-butoxycarbonyl((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)amino)propanoic acid as a gray oil (392 mg, 75%). ESI-MS (M+H+): 484.3. 1H NMR (400 MHz, DMSO-d6) δ: 7.79˜7.72 (m, 2H), 7.62˜7.57 (m, 1H), 7.35˜7.26 (m, 2H), 7.14˜7.08 (m, 1H), 4.49 (s, 2H), 4.41˜4.30 (m, 1H), 3.38˜3.26 (m, 2H), 2.33˜2.26 (t, 2H), 2.23˜2.15 (m, 2H), 1.95˜1.84 (m, 2H), 1.47˜1.28 (m, 11H), 1.27˜1.15 (m, 2H), 1.11˜1.02 (m, 1H), 0.87 (s, 9H).

Provenance & Evidence