Trifluoroacetic acid → N-(2-(2-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16, 19-hexaenamidoethyl)disulfanyl)ethyl)-2-hydroxybenzamide

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Trifluoroacetic acid	HCID 6422	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Doconexent	HCID 445580	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide	HCID 58218979	—
Lösungsmittel	Acetonitrile	HCID 6342	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Produkt	N-(2-(2-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16, 19-hexaenamidoethyl)disulfanyl)ethyl)-2-hydroxybenzamide	HCID 59409965	44,5%

Reaktionsschritte

The TFA salt of N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide (1.08 mmol) was taken up in anhydrous CH3CN (15 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 352 mg, 1.08 mmol), HATU (450 mg, 1.2 mmol) and DIEA (0.550 mL). The resulting reaction mixture was stirred at room temperature for 2 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 (60% EtOAc, 40% pentane) afforded N-(2-(2-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)disulfanyl)ethyl)-2-hydroxybenzamide (280 mg, 44%). Mass calculated for C33H46N2O3S2: 582.3; found: [M+H]+=583.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09085527B2
Quelldatensatz	uspto-grants-2015_07
ORD ID	ord-ea4fe49bc2ae42429d9606da74febedd
Quellennotiz	uspto-grants-2015_07