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Ethyl Acetate → Octadeca-9,12-dienoic acid 3-dimethylamino-2-octadeca-9,12-dienoyloxy-propyl ester

HRID 237181
Notes
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Reaction equation

HRID 237181 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:21][N:22]([CH3:28])[CH2:23][CH:24]([OH:27])[CH2:25]O.CCN=C=N[CH2:34][CH2:35][CH2:36]N(C)C.CCO[C:43]([CH3:45])=[O:44]>CN(C=O)C.C(N(C(C)C)CC)(C)C>[CH3:21][N:22]([CH3:28])[CH2:23][CH:24]([O:27][C:43](=[O:44])[CH2:45][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=[CH:6][CH2:5][CH:4]=[CH:3][CH2:2][CH2:1][CH2:36][CH2:35][CH3:34])[CH2:25][O:19][C:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 790783-(Dimethylamino)-1,2-propanediolHCID 5280450Linoleic Acid

Product 1

HCID 74439361Octadeca-9,12-dienoic acid 3-dimethylamino-2-octadeca-9,12-dienoyloxy-propyl ester

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of the linoleic acid (25 g, 89.1 mmol) in anhydrous DMF (60 mL), diisopropyl ethylamine (17 mL, 100 mml) was added at room temperature with stirring followed by 3-(dimethylamino)-1,2-propanediol (4.8 g, 40.5 mmol) and EDCI (17.25 g, 89.9 mmol) and the mixture was stirred at room temperature overnight. The TLC of the reaction mixture (eluent 20% EtOAc in hexanes) showed the completion of the reaction. The reaction mixture was poured into ice water and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (100 mL), saturated NaHCO3 (100 mL) and dried over Na2SO4. Concentration of the organic layer provided the crude product which was purified by column chromatography (silica gel, eluent: 20% EtOAc in hexanes). The fractions containing pure product was pooled and concentrated. The pure ester was isolated as a clear liquid (5.7 g, 22%). MS m/z 645 (M+H). 1H NMR CDCl3 δ 0.88 (t, J=6.3 Hz, 6H), 1.20-1.39 (m, 28H), 1.61 (t, J=4.9 Hz, 12H), 2.03-2.08 (m, 8H), 2.26-2.38 (m, 10H), 2.44-2.56 (m, 2H), 2.76 (t, J=6.3 Hz, 4H), 4.09 (dd, J=6.1 Hz & 11.9 Hz, 1H), 4.36 (dd, J=3.3 & 11.9 Hz, 1H), 5.29-5.34 (m, 1H), 5.34-5.41 (m, 8H). 13C NMR CDCl3 δ 14.30, 22.79, 25.08, 25.10, 25.83, 27.40, 29.26, 29.30, 29.34, 29.42, 29.55, 29.83, 31.73, 34.32, 34.58, 46.01, 59.37, 64.02, 128.08, 128.24, 130.21, 130.42, 173.39, 173.65.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthe completion of the reaction
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers were washed with water (100 mL), saturated NaHCO3 (100 mL)
  5. dry with materialdried over Na2SO4
  6. customConcentration of the organic layer provided the crude product which
  7. customwas purified by column chromatography (silica gel, eluent: 20% EtOAc in hexanes)
  8. additionThe fractions containing pure product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fd2c285cb6f84ea697e1388fb53f2459
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642076B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes