Reaction #1483035

Reaction equation

TFA

DIEA

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid

HATU

N-(2-aminoethyl)nicotinamide

→

N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)nicotinamide

Solvents

CH3CN

EtOAc

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   WashThe organic layer was washed with saturated aqueous NaHCO3, brine
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherPurification by silica gel chromatography (5% MeOH—CH2Cl2)

Procedure

The TFA salt of N-(2-aminoethyl)nicotinamide (5.0 mmol) was taken up in CH3CN (20 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (5.0 mmol), HATU (5.5 mmol) and DIEA (15 mmol). The resulting reaction mixture was stirred at room temperature for 2 h and diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (5% MeOH—CH2Cl2) afforded N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)nicotinamide. MS calculated for C30H41N3O2: 475.32. found: [M+H]+ 476.

Source