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

HRID 537837노트

반응식

HRID 537837 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.[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 86684848(6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-18-yl 3-(dimethylamino)propyl(hexyl)carbamate수율 78.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 21881112Ethyl ether methylene chloride용매

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 (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).

후처리

  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)

출처 및 근거

ORD 기록
ord-54d244c0f9e34aa59229214964f97422
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865675B2

반응 노트

불러오는 중…