Ethanol → HCID 86700862, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with methyl 2-(1-(4′-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (0.040 g, 0.034 mmol), lithium hydroxide monohydrate (0.043 g, 1.040 mmol), tetrahydrofuran (1 ml), ethanol (0.3 ml) and water (0.3 ml), and stirred at 50° C. for 2 hours. The mixture was purified by HPLC (0.1% NH4OH, 10-50% acetonitrile/water, 20 minutes run, retention time ˜7 minutes) to afford {1-[4′-(5-cyclobutyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid (6 mg, 39%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.89 (m, 5H) 1.89-2.00 (m, 1H) 2.00-2.14 (m, 5H) 2.26-2.39 (m, 5H) 3.62-3.73 (m, 1H) 3.86 (s, 2H) 7.43 (d, J=8.40 Hz, 2H) 7.55 (d, J=8.50 Hz, 2H) 7.62 (s, 4H) 10.39-10.59 (br. s, 1H). LC/MS, [MS+] 459.22, RT: 2.61 (Condition M).

Provenance & Evidence