Acetonitrile → Salicylamide

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).

1. customThe resulting reaction mixture
2. washwashed successively with saturated aqueous NaHCO3 and brine
3. dry with materialThe organic layer was dried (Na2SO4)
4. concentrationconcentrated under reduced pressure
5. customPurification by chromatography (95% CH2Cl25% MeOH)

ORD record

ord-bd226635d5f04053873a3dba29fd4dfd

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09289503B2