Ammonium formate → 3-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(5-chloro-4-hydroxy-6-oxo-6H-pyridazin-1-yl)-3-cyclopentyl-propionic acid (14.5 g, 50.6 mmol) in ethanol (150 mL) was treated with 20% palladium on carbon (50% in water, 1.5 g) and ammonium formate (16 g, 75.9 mmol). The mixture was stirred at reflux for 2 h. At this time, the reaction was cooled to 25° C., filtered, and concentrated in vacuo. Water (50 mL) was added to the residue and the resulting solution was acidified with a 6N aqueous hydrochloric acid solution to pH=2˜3. The solution was extracted with ethyl acetate (2×100 mL). The combined organics were dried over sodium sulfate and concentrated in vacuo to afford 3-cyclopentyl-2-(4-hydroxy-6-oxo-6H-pyridazin-1-yl)-propionic acid as a white solid (12.5 g, 98%).

Provenance & Evidence