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

HRID 869787Notes

Reaction equation

HRID 869787 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]1=[O:17].[C:18](O)(=[O:40])[CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH3:39].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>[O:17]=[C:12]1[CH:13]=[CH:14][C:15](=[O:16])[N:11]1[CH2:10][CH2:9][NH:8][C:18](=[O:40])[CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH3:39]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 445580DoconexentHCID 2778791N-(2-Aminoethyl)maleimideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58348976(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethyl)docosa-4,7,10,13,16,19-hexaenamideYield 70.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  1. customThe resulting reaction mixture
  2. washwashed successively with saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-b031858610d94c349049042050ce494f
Source dataset
uspto-grants-2015_03
Patent number
US08969354B2

Reaction notes

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