Triethylamine → N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine 4-pyridylamide

Participants

Reaction Steps

N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine (4.40 g) was dissolved in dry tetrahydrofuran (100 ml) and triethylamine (1.80 ml) was added under ice-cooling, followed by stirring for 15 minutes. To this solution was added ethyl chlorocarbonate (1.44 g) and the mixture was stirred for 30 minutes. After adding 4-amino-2-chloropyridine (1.54 g), the reaction was carried out at room temperature for 10 hours. Thereafter, the solid was filtered off and the filtrate was concentrated under a reduced pressure. The residue was extracted with ethyl acetate. The extract was purified with a column chromatography (hexane/ethyl acetate=3/1) to obtain N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine 4-(2-chloro)pyridylamide (I) (0.60 g), which was confirmed by the following NMR analysis, in the form of a white powder.

Provenance & Evidence