Sodium Hydroxide → 1-{4'-[5-((R)-1,2-dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

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Reaction Steps

1-{4′-[5-((R)-1,2-Dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid methyl ester (97 mg) was dissolved in 2 mL of THF and 2 mL of ethanol. To this clear solution was added 1N NaOH solution 2 mL. The clear solution was stirred at room temperature overnight. Solvents were evaporated and the residue was dissolved in water (12 mL). The solution was filtered. The filtrate was treated with hydrochloric acid (1N, 2.5 mL). The white precipitate was filtered and dried in air to provide 1-{4′-[5-((R)-1,2-dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid as a pale yellow solid (84 mg, 89.3% yield). LC/MS calcd for C25H28N4O4 (m/e) 448.0, obsd 449.2 (M+H); 1H-NMR (300 MHz, DMSO-d6) δ ppm 0.52 (br, 1H), 0.88 (br, 5H), 1.04-1.25 (m, 5H), 1.35-1.43 (m, 2H), 1.62-1.85 (br, 1H), 3.80 (s, 3H), 4.55 (br, 1H), 7.35 (d, J=8.3 Hz, 2H), 7.57 (d, J=8.3 Hz, 2H), 7.68 (d, J=8.3 Hz, 2H), 7.78 (d, J=8.3 Hz, 2H), 9.34 and 9.67 (br s, 1H), 12.30 (br s, 1H).

Provenance & Evidence