Sodium Hydroxide → (E)-4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoic acid

Participants

Reaction Steps

(E)-Methyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate (200 mg, 0.41 mmol) was taken up in 5 mL of THF along with 2 mL of a 5 N NaOH. The resulting reaction mixture was stirred at room temperature for 1 h, concentrated under reduced pressure to remove the THF, and diluted with water (10 mL). The aqueous layer was acidified to pH=2 with 3 N HCl and then extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford 190 mg of (E)-4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoic acid (97% yield). MS (EI) calcd for C28H40N2O4: 468.30. found 469 (M+1).

Provenance & Evidence