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

HRID 1479323ノート

反応式

HRID 1479323 の反応式
[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]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86682232HCID 86682232、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-41fdbbfaf39a4f16b4580beb28d0aad1
出典データセット
uspto-grants-2016_08
特許番号
US09408914B2

反応ノート

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