Acetonitrile → Salicylamide

Participants

Reaction Steps

tert-Butyl 2-((2-(2-hydroxybenzamido)ethyl)methyl)amino)ethylcarbamate (380 mg, 1.13 mmol) was taken up in 5 mL of a 25% TFA in CH2Cl2 and allowed to stand at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure to afford the TFA salt of N-(2-((2-aminoethyl)(methyl)amino)ethyl)-2-hydroxybenzamide. This material was taken up in 10 mL of CH3CN along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 370 mg, 1.13 mmol), HATU (472 mg, 1.24 mmol) and DIEA (0.59 mL). The resulting reaction mixture was stirred at room temperature for 2 h. It was then diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (95% CH2Cl25% MeOH) afforded 420 mg of N-(2-((2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)methyl)amino)ethyl)-2-hydroxybenzamide. MS (EI) called for C34H49N3O3: 547.38; found: 548 (M+1).

Provenance & Evidence