Diisopropylamine → {2-[3-Chloro-5-(diisopropylcarbamoyl)-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.10 g) in tetrahydrofuran (5 ml) was added DMF (0.005 ml) and oxalyl chloride (0.175 ml). After 0.5 h DIPEA (0.13 ml), diisopropylamine (0.20 ml) and DMAP (0.002 g) were added. After 18 h the mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The combined organic phases were washed with brine and dried over magnesium sulphate. Filtration and evaporation gave the crude product which was purified by flash column chromatography on silica eluting with cyclohexane/ethyl acetate (1:3). This afforded the title compound as a colourless gum (0.078 g).

Provenance & Evidence