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

HRID 85402

반응식

HRID 85402 반응식
C(O)(C(F)(F)F)=O.[NH2:8][CH2:9][CH2:10][S:11][S:12][CH2:13][CH2:14][NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].[C:25](O)(=[O:47])[CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39]/[CH:40]=[CH:41]\[CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH3:46].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CC#N.CCOC(C)=O>[C:25]([NH:8][CH2:9][CH2:10][S:11][S:12][CH2:13][CH2:14][NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])(=[O:47])[CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39]/[CH:40]=[CH:41]\[CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH3:46]

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 445580DoconexentHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58218979N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide

생성물 1

HCID 59409965N-(2-(2-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16, 19-hexaenamidoethyl)disulfanyl)ethyl)-2-hydroxybenzamide수율 44.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  1. customThe resulting reaction mixture
  2. washwashed successively with saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography (60% EtOAc, 40% pentane)

출처 및 근거

ORD 기록
ord-8d1160eaa5fd4af194dda72e6dc6a36f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846972B2

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