反应详情

(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).

1. customThe resulting reaction mixture
2. concentrationconcentrated under reduced pressure
3. customto remove the THF
4. additiondiluted with water (10 mL)
5. extractionextracted with EtOAc
6. washThe combined organic layers were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure