Reaktion #172587

Reaktionsgleichung

TFA

DIEA

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

HATU

1-(2-aminoethyl)-1H-pyrrole-2,5-dione

→

(4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethyl)docosa-4,7,10,13,16,19-hexaenamide

Ausbeute 70.6%

Lösungsmittel

CH3CN

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   Waschenwashed successively with saturated aqueous NaHCO3 and brine
3. 3
   TrocknenThe organic layer was dried over Na2SO4
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigePurification by chromatography (CH2Cl2)

Vorschrift

The TFA salt of 1-(2-aminoethyl)-1H-pyrrole-2,5-dione (Aldrich, 280 mg, 1.10 mmol) was taken up in CH3CN (10 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (360 mg, 1.1 mmol), HATU (460 mg, 1.2 mmol) and DIEA (0.58 mL). The resulting reaction mixture was stirred at room temperature for 3 h. It was then diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by chromatography (CH2Cl2) afforded (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethyl)docosa-4,7,10,13,16,19-hexaenamide (350 mg, 70%).

Quelle