Potassium Carbonate → 4-Bromo-2-((1-carboxyethyl)amino)-5-fluorobenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-amino-4-bromo-5-fluorobenzoic acid, hydrochloride (D85) (1.5 g, 5.55 mmol) in water (10 mL) was added sodium hydroxide (0.444 g, 11.09 mmol) followed by potassium carbonate (1.533 g, 11.09 mmol). A solution of methyl 2-bromopropionate (0.619 mL, 5.55 mmol) in MeOH (10.00 mL) was added to the mixture and the mixture was then heated at 80° C. for 24 hours. LCMS showed reaction was not complete with remaining significant amount of starting material. Further methyl 2-bromopropionate (0.619 mL, 5.55 mmol) was added to the mixture and the mixture was then stirred for 24 hours at 80° C. 6M aqueous sodium hydroxide (4.62 mL, 27.7 mmol) was added to the mixture and the mixture was then heated at 100° C. for 1.5 h. After cooling to RT, MeOH was removed under reduced pressure. The aqueous residue was extracted with ethyl acetate (20 mL). The aqueous layer was cooled to 0° C. and was then acidified with addition of concentrated HCl. The formed precipitate was filtered, washed with water and collected to give title compound (1.78 g). LCMS (A): m/z (M+H)+ 306/308, C10H9BrFNO4 requires 305/307 (acidic).

Provenance & Evidence