Hydrochloric Acid → HCID 46223054, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionic acid methyl ester (1.70 g, 4.96 mmol) in methanol (8.3 mL, 0.6M) was treated with a 4N aqueous sodium hydroxide solution (1.37 mL, 5.46 mmol) and was stirred at 25° C. for 4 h. After this time, the reaction was poured into water (150 mL) which was acidified with a 3N aqueous hydrochloric acid solution and then was extracted into 90/10 methylene chloride/methanol (3×100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionic acid (1.60 g, 98%) as a white solid; ES+-HRMS m/e calcd for C18H20N2O4 [M+H+] 329.1496, found 329.2496. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.11 (br s, 2H), 1.35-1.78 (m, 7H), 1.86-2.05 (m, 1H), 2.10-2.25 (m, 1H), 5.31 (dd, J=10.9, 4.2 Hz, 1H), 5.73 (d, J=2.7 Hz, 1H), 7.30 (d, J=7.5 Hz, 2H), 7.37 (t, J=7.5 Hz, 1H), 7.53 (t, J=7.5 Hz, 2H), 8.10 (d, J=2.7 Hz, 1H), 13.02 (br s, 1H).

Provenance & Evidence