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

HRID 237181

反応式

HRID 237181 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fd2c285cb6f84ea697e1388fb53f2459
出典データセット
uspto-grants-2014_02
特許番号
US08642076B2

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