Sodium Hydroxide → 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (Intermediate 73, Step 2, 1.78 g, 4.73 mmol) in tetrahydrofuran (13 mL, 0.36M) was treated with a 4N aqueous sodium hydroxide solution (1.3 mL, 5.2 mmol) and stirred at 25° C. overnight. After this time, the reaction was concentrated in vacuo and the residue was diluted with water (50 mL) and was then acidified with a 1N aqueous hydrochloric acid solution. The precipitate was filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid (1.45 g, 85%) as an off-white solid; ES+-HRMS m/e calcd for C12H15N2O3I [M+H+] 363.0200, found 363.0197. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.18 (m, 2H), 1.36-1.75 (m, 7H), 1.88-2.02 (m, 1H), 2.17 (ddd, J=13.9, 10.8, 5.1 Hz, 1H), 5.30 (dd, J=10.8, 4.3 Hz, 1H), 7.65 (d, J=1.9 Hz, 1H), 8.23 (d, J=1.9 Hz, 1H), 13.10 (s, 1H).

Provenance & Evidence