1,2-Dichloroethane → 4-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-quinoline-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To a solution of 2 g of 4-Carboxymethoxy-quinoline-2-carboxylic acid ethyl ester in 20 ml of DMF, 2.8 g of EDC, 2.7 g of pentafluorophenol was added and the reaction mixture was stirred at RT for 2 h. Then, 3.1 g of (S)-Pyrrolidine-2-carboxylic acid cyclobutylamide trifluoroacetate and 1.7 g of NEM in 10 ml of DMF was added. After 16 h the reaction mixture was diluted with water and extracted with DCM (3×150 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 1.4 g.

Provenance & Evidence