Pyridine → (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-18-yl 3-(dimethylamino)propyl(hexyl)carbamate

HRID 537837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537837
[CH2:1]([CH:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37]C)[OH: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].N1C=CC=C[CH:40]=1.O=C(Cl)[O:47][C:48](Cl)(Cl)Cl.[CH2:53]([NH:59][CH2:60][CH2:61][CH2:62][N:63]([CH3:65])[CH3:64])[CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>CCOCC.CCOCC.ClCCl>[CH3:64][N:63]([CH3:65])[CH2:62][CH2:61][CH2:60][N:59]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:48](=[O:47])[O:20][CH:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH3:40])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 10426DiphosgeneHCID 28878850N-hexyl-N',N'-dimethylpropane-1,3-diamineHCID 44468963Dlin-MeOH

Produkt 1

HCID 86684848(6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-18-yl 3-(dimethylamino)propyl(hexyl)carbamateAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 21881112Ethyl ether methylene chlorideLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a solution of dilinoleyl methanol (1.0 g, 1.9 mmol) and pyridine (230 μL, 4.7 mmol) in anhydrous ether (10 mL) cooled to −15° C. under nitrogen was slowly added diphosgene (380 μL, 3.1 mmol). The reaction was stirred for 20 minutes at −15° C., then N-hexyl-N′,N′-dimethylpropane-1,3-diamine (3.8 g, 20.3 mmol) was added as a solution in 4:1 ether/dichloromethane (10 mL). The solution was warmed to room temperature and stirring was continued for 20 minutes. Upon completion, the solution was diluted with diethyl ether (100 mL) and washed with saturated sodium bicarbonate (2×50 mL). The ether extract was dried on magnesium sulphate, filtered, concentrated in vacuo to dryness. The residue was purified by column chromatography (100% ethyl acetate) to afford the title compound as a colorless oil (1.1 g, 76%). 1H NMR (400 MHz, CDCl3): δ 5.43-5.26 (m, 8H), 4.80-4.68 (m, 1H), 3.35-3.15 (m, 4H), 2.81-2.75 (m, 4H), 2.66-2.25 (m, 8H), 2.10-1.70 (m, 14H), 1.64-1.46 (m, 6H), 1.40-1.20 (m, 38H), 1.00-0.93 (m, 3H), 0.92-0.86 (m, 6H).

Aufarbeitung

  1. temperatureThe solution was warmed to room temperature
  2. stirringstirring
  3. waitwas continued for 20 minutes
  4. washwashed with saturated sodium bicarbonate (2×50 mL)
  5. extractionThe ether extract
  6. customwas dried on magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to dryness
  9. customThe residue was purified by column chromatography (100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-54d244c0f9e34aa59229214964f97422
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865675B2

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