Ethanolamine → N-(2-Hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide

HRID 869786Notes

Reaction equation

HRID 869786 reaction equation
[C:1]([OH:24])(=O)[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22].[CH2:25]([CH2:27][NH2:28])[OH:26].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>[OH:26][CH2:25][CH2:27][NH:28][C:1](=[O:24])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 445580DoconexentHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 5283451N-(2-Hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 1.2 g, 3.66 mmol) was taken up in 20 mL of CH3CN along with ethanolamine (220 μL, 3.66 mmol), HATU (1.5 g, 4.0 mmol) and DIEA (950 μL, 5.49 mmol). The resulting reaction mixture was stirred at room temperature for 2 h and then diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, brine, dried (Na2SO4) and concentrated under reduced pressure to afford crude (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide. This material was taken up in 15 mL of CH2Cl2 along with (E)-methyl 4-chloro-4-oxobut-2-enoate (3.66 mmol) and triethylamine (765 μL, 5.49 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with CH2Cl2 and washed with brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (60% EtOAc, 40% pentane) afforded 380 mg of 2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl methyl fumarate (21% yield). MS (EI) calcd for C29H41NO5: 483.3. found: 484 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with saturated aqueous NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b1dc57263a24c2b9037198d4f1ee398
Source dataset
uspto-grants-2015_03
Patent number
US08969354B2

Reaction notes

Loading…