Reacción #956964

Ecuación de reacción

HCl

DIEA

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

HATU

(E)-methyl 4-(2-aminoethylamino)-4-oxobut-2-enoate

→

(E)-methyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate

Rendimiento 35.8%

Disolventes

CH3CN

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   LavadoThe organic layer was washed with saturated aqueous NaHCO3, brine
3. 3
   Secadodried (Na2SO4)
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroPurification by chromatography (95% CH2Cl2, 5% MeOH)

Procedimiento

The HCl salt of (E)-methyl 4-(2-aminoethylamino)-4-oxobut-2-enoate (8.1 mmol) was taken up in 40 mL of CH3CN along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 2.66 g, 8.1 mmol), HATU (3.4 g, 12.1 mmol) and DIEA (4.2 mL). 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 (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (95% CH2Cl2, 5% MeOH) afforded 1.4 g of (E)-methyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate. MS (EI) calcd for C29H42N2O4: 482.31. found 483 (M+1).

Fuente