Hydrochloric Acid → HCID 66751043, compound

Participants

Reaction Steps

To a stirred solution of methyl 4-[(4-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}-2,6-dioxopiperidin-1-yl)methyl]benzoate (Example 74, 0.575 g, 1.11 mmol) in THF (5 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 1 h the reaction mixture was warmed to room temperature and kept stirring for 3 h. The mixture was acidified with 1 M hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to provide the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 20:80) to provide 4-[({5-[4-(2-tert-butylphenyl)piperazin-1-yl]-3-(carboxymethyl)-5-oxopentanoyl}amino)methyl]benzoic acid (0.608 g, quant) as a white solid.

Provenance & Evidence