Benzoic Acid → methyl N-((6-chloro-4-hydroxy-2-oxo-1'-(phenylcarbonyl)-spiro[naphthalene-1,4'-piperidin]-3-yl)carbonyl)glycinate

Participants

Reaction Conditions

Reaction Steps

A solution of the hydrochloride salt of methyl N-((6-chloro-4-hydroxy-2-oxo-spiro[naphthalene-1,4′-piperidin]-3-yl)carbonyl)glycinate (0.050 g, 0.12 mmol) and Hunig's base (0.024 mL, 0.14 mmol) in DMF/DMSO (2:1, 1.5 mL) was stirred at 25° C. for 5 minutes. A mixture of benzoic acid (0.067 g, 0.54 mmol) and N-(3-dimethylaminopropyl)-n′-ethylcarbodiimide hydrochloride (0.13 g, 0.65 mmol) in DMF (1 mL) was added. The mixture was stirred at 60° C. for 8 hours. The solution was diluted with EtOAc (20 mL), and washed with brine (2×25 mL). The organic layer was dried over MgSO4, concentrated, and purified by flash column chromatography (silica, 0-1% MeOH in DCM) to give methyl N-((6-chloro-4-hydroxy-2-oxo-1′-(phenylcarbonyl)-spiro[naphthalene-1,4′-piperidin]-3-yl)carbonyl)glycinate. MS m/e=483.5 (M+H)+.

Provenance & Evidence