Trifluoroacetic acid → (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

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Trifluoroacetic acid	HCID 6422	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Doconexent	HCID 445580	—
Edukt	N-(2-Aminoethyl)maleimide	HCID 2778791	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Lösungsmittel	Acetonitrile	HCID 6342	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Produkt	(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	HCID 58348976	70,6%

Reaktionsschritte

The TFA salt of 1-(2-aminoethyl)-1H-pyrrole-2,5-dione (Aldrich, 280 mg, 1.10 mmol) was taken up in 10 mL of CH3CN along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 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 (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (CH2Cl2) afforded 350 mg of (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 (70% yield).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09289503B2
Quelldatensatz	uspto-grants-2016_03
ORD ID	ord-c5c2c63da544479ab7b18dbdbf39a652
Quellennotiz	uspto-grants-2016_03