Hydrochloric Acid → HCID 11363729, compound

Participants

Reaction Steps

1.137 cm3 of a 5 N aqueous sodium hydroxide solution are added at a temperature in the region of 20° C. to 0.0675 g (0.135 mmol) of the enantiomer B (dextrorotatory) of methyl 1-[(2E)-3-(2,5-difluorophenyl)-2-propenyl]-3-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-3-pyrrolidinecarboxylate in solution in 3 cm3 of dioxane. After stirring under reflux for 48 hours, the reaction medium is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 2 cm3 of water and 5 cm3 of dichloromethane. The aqueous phase is acidified with 1 N and then 0.1 N hydrochloric acid to a pH value of 7. The aqueous phase is extracted with twice 5 cm3 of dichloromethane. The organic phases are combined, washed with 5 cm3 of water, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.035 g of the enantiomer B of 1-[(2E)-3-(2,5-difluorophenyl)-2-propenyl]-3-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-3-pyrrolidinecarboxylic acid (absolute configuration not determined) in the form of a beige solid melting at 80–84° C.

Provenance & Evidence