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

https://huagongshe.com/ko/reaction/85402

참여 물질

역할	이름	HCID	투입량
반응물	Trifluoroacetic acid	HCID 6422	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	Doconexent	HCID 445580	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide	HCID 58218979	—
용매	Acetonitrile	HCID 6342	—
용매	Ethyl Acetate	HCID 8857	—
생성물	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%

반응 단계

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.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08846972B2
출처 데이터셋	uspto-grants-2014_09
ORD ID	ord-8d1160eaa5fd4af194dda72e6dc6a36f
출처 메모	uspto-grants-2014_09