Trifluoroacetic acid → N,N-bis(2-((Z)-Octadec-9-enoyloxy)ethyl)amine

HRID 1479323노트

반응식

HRID 1479323 반응식
[C:1]([O:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])C(=O)OC(C)(C)C)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].FC(F)(F)C(O)=O>ClCCl>[C:1]([O:20][CH2:21][CH2:22][NH:23][CH2:31][CH2:32][O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86682232HCID 86682232, 화합물

생성물 1

HCID 86682231N,N-bis(2-((Z)-Octadec-9-enoyloxy)ethyl)amine수율 94.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The resulting tert-butyl N,N-bis(2-((Z)-octadec-9-enoyloxy)ethyl)carbamate (1.22 g, 1.66 mmol) was dissolved in dichloromethane (30 mL), and stirred at room temperature for 3.5 hours after adding trifluoroacetic acid (2.56 mL, 33.2 mmol). The aqueous layer was extracted with chloroform after adding a saturated sodium bicarbonate aqueous solution to the reaction solution. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 96/4) to give compound 73 (998 mg, 94.6%).

후처리

  1. extractionThe aqueous layer was extracted with chloroform
  2. additionafter adding a saturated sodium bicarbonate aqueous solution to the reaction solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationafter filtration
  7. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 96/4)

출처 및 근거

ORD 기록
ord-41fdbbfaf39a4f16b4580beb28d0aad1
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09408914B2

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