Реакция #956979

Уравнение реакции

HATU

(S)-tert-butyl 2-amino-6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)hexanoate

monomethyl fumarate

DIEA

→

(S)-tert-butyl 6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)-2-((E)-4-methoxy-4-oxobut-2-enamido)hexanoate

Выход 30.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   ДругоеThe resulting reaction mixture
2. 2
   Концентрированиеconcentrated under reduced pressure
3. 3
   Промывкаwashed with water and brine
4. 4
   СушкаThe organic layer was dried over Na2SO4
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеPurification by silica gel chromatography (EtOAc/pentane)

Методика

The crude (S)-tert-butyl 2-amino-6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)hexanoate, prepared above, was taken up in 40 mL acetonitrile along with monomethyl fumarate (610 mg, 4.69 mmol), DIEA (3.0 mL, 18.8 mmol) and HATU (2.4 g, 6.39 mmol). The resulting reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The resulting residue was taken up in 100 mL of EtOAc and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by silica gel chromatography (EtOAc/pentane) afforded (S)-tert-butyl 6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)-2-((E)-4-methoxy-4-oxobut-2-enamido)hexanoate (500 mg, 30%).

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