Ethylmorpholine → 4-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of 1.30 g 4-((R)-1-Carboxy-ethoxy)-7-methyl-quinoline-2-carboxylic acid in 10 ml DCM, 1.24 g pentafluorophenol and 1.29 g EDC were added. The mixture was stirred under exclusion of moisture until LCMS indicated complete conversion to the corresponding pentafluorophenolester. (S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochloride (1.10 g) was mixed with 1.1 ml N-ethylmorpholine and 5 ml DCM and this mixture added dropwise to the solution of the pentafluorophenolester. After 12 h the reaction mixture was diluted with water and extracted with DCM. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica eluting with ethyl acetate/heptane gradient. Yield: 1.40 g.

Provenance & Evidence