Oxalyl chloride → HCID 54300940, compound

Participants

Reaction Steps

2M Oxalyl chloride solution in dichloromethane (0.600 ml) and DMF (0.01 ml) were added to a suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.393 g) in anhydrous dichloromethane (5 ml). The reaction was stirred at room temperature for 1 h then a solution of 4-(2-fluoro-phenylamino)-butyric acid methyl ester (0.422 g) in dichloromethane (1.5 ml), DMAP (0.006 g) and DIPEA (0.522 ml) were added. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was removed and the organic phase washed with 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, water and dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with ethyl acetate:cyclohexane (4:1 v/v), to give the title compound as a colourless gum (0.287 g).

Provenance & Evidence