Methyl 3-chlorocarbonylpropenoate → (S,E)-N-(a-ethylbenzyl)-3-[2-(3-methoxycarbonylpropenoyl)aminoethoxy]-2-phenylquinoline-4-carboxamide

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Reaction Conditions

Reaction Steps

1.4 g (3.3 mmol) of (S)-N-(α-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide (compound of Description 4) were dissolved, under nitrogen atmosphere, in 35 ml of dry CH2Cl2; 0.77 ml (5.5 mmol) of TEA were added, the solution was cooled to 0° C. and 0.4 g (3.4 mmol) of methyl 3-chlorocarbonylpropenoate (compound of Description 5), dissolved in 25 ml of CH2Cl2, were added dropwise. The reaction was stirred at room temperature for 2 days, washed with H2O, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl, dried over Na2SO4 and evaporated in vacuo to dryness. The residue was purified by gradient flash column chromatography on 230-400 mesh silica utilising a mixture of hexane/EtOAc 8:2 as starting eluent and a mixture of hexane/EtOAc 3:7 as final eluent. The crude product so obtained was further purified by preparative HPLC to yield 0.30 g of the title compound.

Provenance & Evidence