Sodium Hydroxide → HCID 10276607, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in Example 25B-a, 45 mg, 0.094 mmol) in methanol (500 μL) was treated with a 1N aqueous sodium hydroxide solution (188 μL, 0.188 mmol). The reaction mixture was heated under reflux for 1 h and then allowed to cool to 25° C. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 15/1 methylene chloride/methanol) afforded 6-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionylamino]-nicotinic acid (15 mg, 34%) as a pale yellow solid: mp 155-158° C.; FAB-HRMS m/e calcd for C30H28N2O3 (M+H)+ 465.2178, found 465.2169.

Provenance & Evidence