Dansyl chloride → Tert-butyl 3-((3-(3(((5-(dimethylamino)naphthalen-1-yl)(methyl)amino)methyl)phenoxy)propyl)(methyl)amino)-propanoate

Participants

Reaction Steps

The NaHCO3 solution (133 mg, 1.58 mmol) in water (2 mL) is added at RT to the solution of crude tert-butyl 3-(methyl(3-(3-((methylamino)methyl)phenoxy)propyl)amino)propanoate (455 mg, 1.35 mmol) and of dansyl chloride (364 mg, 1.35 mmol) in acetonitrile (35 mL). This mixture is stirred for 1 h 30 at the same temperature under argon. And the solvent is then evaporated under reduced pressure and the obtained oil is purified by chromatography on silica gel (eluent—DCM followed by the mixture DCM:MeOH=100:1). The final product is obtained as a fluorescent pale green amorphous gum (522 mg, 68%).

Provenance & Evidence