Diisopropylethylamine → Tert-butyl (2-(7-oxo-7-((pyridin-3-ylmethyl)amino)heptanamido)phenyl)carbamate

Participants

Reaction Steps

To a solution of 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acid (1.2 g, 3.42 mmol) in DMF (10 mL) were added HBTU (1.43 g, 3.76 mmol), DIEA (1.3 g, 10.3 mmol) at room temperature. The resulting mixture was stirred for 10 min, then tpyridin-3-ylmethanamine (1.43 g, 3.76 mmol) was added to the reaction solution. The reaction mixture was stirred for 12 h at room temperature. The reaction was quenched with water (100 mL). The resulting mixture was extracted by EtOAc (100 mL×2). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The resulting solid was purified by column chromatography (elute: EtOAc:MeOH=100:1) to afford desired compound (1.2 g, yield 79.7%) as an off-white solid.

Provenance & Evidence