Water → trans-(R)-3-(4-(((4-tert-butylcyclohexyl)(1-methyl-1H-benzo[d]imidazol-2-yl)amino)methyl)benzamido)-2-hydroxypropanoic acid

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Reaction Conditions

Reaction Steps

To a solution of the title compound of Example 7 (0.1 mmol, 50 mg) in 2 mL of MeOH was added LiOH (0.5 mmol, 12 mg). H2O was added dropwise until the reaction became slightly cloudy, then the mixture was sonicated to dissolve the LiOH. The reaction was stirred at 40° C. for 2 h. The reaction was concentrated under reduced pressure and the residue was taken up in dioxane/H2O and acidified with TFA. Purification by reverse-phase HPLC (Condition A), followed by lyophilization, afforded the title compound as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.79 (d, 2H), 7.58 (m, 1H), 7.39-7.52 (overlapping m, 5H), 4.86 (s, 2H), 4.34 (m, 1H), 3.87 (s, 3H), 3.52-3.84 (overlapping m, 3H), 2.16 (m, 2H), 1.99 (m, 2H), 1.84 (m, 2H), 1.31 (m, 2H), 1.14 (m, 1H), 0.92 (s, 9H). MS (ESI): m/z 487 (M+H). MS (ESI): m/z 507 (M+H). HPLC A: 1.84 min.

Provenance & Evidence