Methanol → HCID 178522245, compound

Participants

Reaction Conditions

Reaction Steps

Lithium hydroxide monohydrate (184 mg, 4.38 mmol) was added in one portion to a solution of ethyl cis-4-{4-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-phenoxy}cyclohexanlecarboxylate (Example 645, 221 mg, 0.44 mmol) in a mixture of THF (4 mL), H2O (4 mL) and MeOH (8 mL) and the reaction mixture was stirred at 35° C. for 3 h. The reaction mixture was concentrated in vacuo and citric acid (40 mL) was added. The resulting mixture was filtered, washed with H2O and recrystallised from ethanol/H2O to give the title compound as a pale yellow solid (118 mg, 56%); 1H NMR δ 1.66-1.70 (4H, m), 1.75-1.83 (4H, m), 2.33-2.40 (1H, m), 4.50 (1H, s), 6.96 (2H, d), 7.67-7.74 (3H, m), 8.17 (1H, q), 10.95 (1H, s), 11.10 (1H, s), 12.05 (1H, s); MS m/e (M−H)− 475. The compound may be further recrystallised from EtOH, melting point 251-253° C.

Provenance & Evidence