Water → HCID 67820811, compound

Participants

Reaction Steps

A solution of 0.85 g of N,N'-carbonyldiimidazole in 10 cm3 of anhydrous dichloromethane is added dropwise, at a temperature close to 20° C., to a solution of 0.87 g of 2-quinolinecarboxylic acid in 15 cm3 of anhydrous dichloromethane. The suspension obtained is stirred for 3 hours at a temperature close to 20° C. and a solution of 2.6 g of tert-butyl 2-(2-amino-N-phenylacetamido)acetate in 25 cm3 of anhydrous dichloromethane is then added. The reaction mixture is stirred for 16 hours at a temperature close to 20° C. and 50 cm3 of water are then added. The aqueous phase is separated off by decanting and then reextracted with twice 15 cm3 of 1,2-dichloroethane. The organic phases are combined, washed with twice 25 cm3 of a saturated aqueous sodium bicarbonate solution and then with twice 25 cm3 of distilled water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization of the residual solid from a mixture of cyclohexane and ethyl acetate (90/10 by volume), 0.8 g of tert-butyl 2-(N-phenyl-2-quinolinecarboxamidoacetamido)acetate melting at 114° C. is obtained.

Provenance & Evidence