Pyridine → (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-18-yl 2-(dimethylamino)ethyl(ethyl)carbamate

HRID 537838노트

반응식

HRID 537838 반응식
[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.[CH3:53][N:54]([CH3:60])[CH2:55][CH2:56][NH:57][CH2:58][CH3:59]>CCOCC>[CH3:53][N:54]([CH3:60])[CH2:55][CH2:56][N:57]([CH2:58][CH3:59])[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]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 10426DiphosgeneHCID 671622-EthylaminoethyldimethylamineHCID 44468963Dlin-MeOH

생성물 1

HCID 86684844(6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-18-yl 2-(dimethylamino)ethyl(ethyl)carbamate수율 78%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
-15 °C

실험 절차

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 (0.38 mL, 3.14 mmol). The reaction was stirred for 1 hour at −15° C., then N,N-dimethyl-N′-ethyl-ethylenediamine (2.2 mL, 14.2 mmol) was added. The solution was warmed to room temperature and stirred for 30 minutes. The solution was diluted with diethyl ether (50 mL) and filtered to remove the urea and ammonium salts. The ether filtrate was concentrated in vacuo to dryness and the residue was purified by column chromatography (100% ethyl acetate) to afford the title compound as a colorless oil (990 mg, 78%). 1H NMR (400 MHz, CDCl3): δ 5.41-5.27 (m, 8H), 4.77-4.69 (m, 1H), 3.55-3.20 (m, 4H), 2.79-2.72 (m, 4H), 2.72-2.56 (m, 1H), 2.55-2.21 (m, 7H), 2.08-1.96 (m, 8H), 1.58-1.44 (m, 4H), 1.39-1.15 (m, 36H), 1.10 (t, J=7.0 Hz, 3H), 0.90-0.82 (m, 6H).

후처리

  1. temperatureThe solution was warmed to room temperature
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. customto remove the urea and ammonium salts
  5. concentrationThe ether filtrate was concentrated in vacuo to dryness
  6. customthe residue was purified by column chromatography (100% ethyl acetate)

출처 및 근거

ORD 기록
ord-7be61616716549a49cbd210749617c30
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865675B2

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