N,N-Dimethylglycine → 3-[5-((3R)-5-oxopyrrolidin-3-yl)-2-chlorophenoxy]benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of (4R)-4-(3-bromo-4-chlorophenyl)pyrrolidin-2-one (0.1 g, 0.36 mmol) and methyl 3-hydroxybenzoate (0.055 g, 0.36 mmol) in dioxane (1 mL) was added N,N-dimethylglycine (0.011 g, 0.11 mmol), copper(I) iodide (0.02 g, 0.11 mmol) and cesium carbonate (0.23 g, 0.72 mmol). The mixture was stirred overnight at 100° C. The mixture was then diluted with ethyl acetate (50 mL), washed with a 10% aq. HCl solution then brine, and concentrated to give 3-[5-((3R)-5-oxopyrrolidin-3-yl)-2-chlorophenoxy]benzoic acid, which was treated with HCl as described for the preparation of (3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid hydrochloride to provide the title compound (22). MS (ESI) m/z 350.07 (M+H)+.

Provenance & Evidence