Sodium Hydroxide → (4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acid

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Reaction Steps

To a solution of (4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester (15 mg, 0.031 mmol) in THF (2 mL) and ethanol (2 mL) was added a 1.0 M solution of sodium hydroxide (310 μL, 0.31 mmol) at room temperature. The resulting colorless solution was stirred for 15 h at which time TLC analysis indicated the absence of the starting material. Then, the solvent was removed under vacuum and the basic aqueous layer was neutralized with 1 N HCl. The resulting solids were collected by filtration and washed with water and hexanes. After air drying, (4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acid (10 mg, 71% yield) was isolated as a white solid. 1H NMR (DMSO-d6) δ ppm 12.04 (br. s., 1H), 9.85 (br. s., 1H), 7.62 (d, J=7.3 Hz, 2H), 6.84-7.54 (m, 7H), 5.78 (br. s., 1H), 3.83 (s, 3H), 2.16 (d, J=6.8 Hz, 2H), 1.65-1.93 (m, 5H), 1.39-1.64 (m, 5H), 1.01-1.35 (m, 3H). LC/MS calcd. for C26H30N4O4 (m/e) 462, obsd. 463.3 [M+H, ES+].

Provenance & Evidence