Sodium Hydroxide → 6-(2-Biphenyl-4-yl-3-cyclopentyl-propionylamino)-nicotinic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 6-(2-biphenyl-4-yl-3-cyclopentyl-propionylamino)-nicotinic acid methyl ester (prepared in Example 22, 100 mg, 0.23 mmol) in methanol (2 mL) was treated with a 1N aqueous sodium hydroxide solution (350 mL, 0.35 mmol). The reaction mixture was heated under reflux for 30 min and then allowed to cool to 25° C. The reaction mixture was then concentrated in vacuo. The resulting residue was partitioned between water and ethyl acetate, and the layers were separated. The aqueous layer was further extracted with ethyl acetate (1×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate then 100% methanol) afforded 6-(2-biphenyl-4-yl-3-cyclopentyl-propionylamino)-nicotinic acid (27 mg, 28%) as a white solid: mp 271-272° C. (dec); FAB-HRMS m/e calcd for C26H26N2O3 (M+H)+ 415.2021, found 415.2010.

Provenance & Evidence