Ethyl bromoacetate → (S)-N-(alpha-ethylbenzyl)-3-(ethoxycarbonylmethoxy)-2-phenylquinoline-4-carboxamide

Participants

Reaction Steps

2.0 g (5.2 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1) were dissolved, under nitrogen atmosphere and magnetic stirring, in 20 ml of THF. 2.0 g (14.5 mmol) of K2CO3, 0.87 ml (7.8 mmol) of ethyl bromoacetate and a small amount of Ki were added and the reaction mixture was left at room temperature under magnetical stirring for 2.5 hours. The precipitate was filtered off and the solution was evaporated in-vacuo to dryness; the residue was dissolved in water and extracted with EtOAc; the organic phase was separated, dried over Na2SO4 and evaporated in-vacuo to dryness to obtain 3.3 g of a dense yellow oil. The oil was purified by flash chromatography on 230-400 mesh silica gel, eluting with a mixture of hexane/EtOAc 70:30 containing 0.5% of 28% NH4OH, and the purified product was triturated with i-Pr2O/i-PrOH to yield 2.1 g of the title compound as a white solid.

Provenance & Evidence