Pyridine → HCID 67890755, compound

Participants

Reaction Steps

Anhydrous dichloromethane (50 ml), 3-(ethyl(phenyl)amino)-3-oxo-propanoic acid (IV) (2.634 g, 12.71 mmol) and pyridine (2.8 ml, 34.66 mmol) were added to a round bottomed flask at 20-25° C. under nitrogen atmosphere, and the resulting mixture was stirred at r.t. for 0.5 h, then cooled to 0-5° C. while stirring. Pivaloyl chloride (2.1 ml, 17.32 mmol) was added dropwise while keeping the temperature below 5° C., and the mixture was further stirred for 1 h at 0-5° C. A solution of methyl 2-chloro-6-methylamino-benzoate (II) (2.3064 g, 11.55 mmol) in anhydrous dichloromethane (11 ml) was prepared and added to the reaction at 0° C. The reaction was allowed to warm up to r.t. and stirred at this temperature for 14 h, then concentrated under reduced pressure. Ethyl acetate (180 ml) and a solution of 0.1N HCl (80 ml) were added, the phases were mixed and the aqueous phase was discharged. The wash steps with 0.1N HCl (80 ml) was repeated twice more, then the reaction was washed twice with 80 ml brine and three times with 80 ml NaHCO3. The organic phases were dried over sodium sulfate and filtered and the solvent was removed under reduced pressure to afford a residue, which was recrystallized from isopropanol to obtain an off-white solid. Yield: 80%. The purity of the isolated product was 100% (HPLC, area %).

Provenance & Evidence