Succinic anhydride → (S)-N-(alpha-ethylbenzyl)-3-[2-(3-carboxypropanoyl)aminoethoxy]-2-phenylquinoline-4-carboxamide

Participants

Reaction Steps

2.0 g (4.7 mmol) of (S)-N-(α-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide (compound of Description 4) and 0.6 g (6.2 mmol) of succinic anhydride were dissolved in 50 ml of toluene; some triturated molecular sieves were added and the reaction mixture was refluxed in a Dean Stark apparatus for 4 hours. The reaction mixture was evaporated in vacuo to dryness, dissolved in 100 ml of CH2Cl2 and washed with sat. sol. NaCl, 20% citric acid and sat. sol. NaCl. The organic layer was dried over Na2SO4 and evaporated in vacuo to dryness to yield 2.3 g of the crude product which was purified by flash column chromatography on 230-400 mesh silica gel, eluting initially with a mixture of CH2Cl2/MeOH 9:1 and then with a mixture of CH2Cl2/MeOH 8:2. The crude solid obtained was triturated with i-Pr2O/i-PrOH, washed and dried to yield 1.4 g of the title compound.

Provenance & Evidence