Methanol → 3,5-Dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoic acid

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Reaction Steps

A solution of aqueous 2N NaOH (2.00 ml) is added to a stirred solution of ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate (0.11 g, 269.28 μmol) in THF:MeOH (2.4 ml:1.2 ml). After 16 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 7 with 1N HCl, and extracted twice with ethyl acetate. The organic layers are combined with aqueous layer and concentrated under reduced pressure. The resulting solids are triturated with 1:1 mixture of acetonitrile and ethanol to give white slurry that is filtered through Celite™ bed. The filtrate is concentrated under reduced pressure and the precipitate is triturated with acetone and filtered to afford the title compound as an off-white solid (99 mg, 99%). Mass spectrum (m/z): 381.2 (M+1).

Provenance & Evidence