Triethylamine → N-(2-azidoethyl)tetradecanamide

HRID 384186

反応式

HRID 384186 の反応式
[N:1]([CH2:4][CH2:5][NH2:6])=[N+:2]=[N-:3].C(N(CC)CC)C.[C:14](Cl)(=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[N:1]([CH2:4][CH2:5][NH:6][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N+:2]=[N-:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 66986Myristoyl chloride

生成物 1

HCID 57914356N-(2-azidoethyl)tetradecanamide収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a 25 mL round-bottomed flask equipped with a magnetic stir bar was added 2-azidoethanamine (0.102 g, 1.18 mmol), DCM (5 mL) and then triethylamine (0.239 g, 2.37 mmol). To this reaction mixture, tetradecanoyl chloride (0.292 g, 1.18 mmol) was added dropwise and allowed to stir at room temperature for 24 hr. Then, the reaction mixture was concentrated de vacuo and then purified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane) to give N-(2-azidoethyl)tetradecanamide (0.245 g, 79% yield). 1H NMR (300 MHz, CDCl3) δ 5.86 (s, 1H), S 3.42 (s, 4H), δ 2.18 (t, 2H), δ 1.62 (m, 2H), δ 1.24 (m, 20H), δ 0.87 (t, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 173.7, 51.2, 39.1, 36.9, 32.1, 29.9, 29.8, 29.7, 29.6, 29.5, 25.9, 22.9, 14.4 ppm; HRMS (ESI) calcd for C16H32N4O (M+) 296.2576, found 296.2566.

後処理

  1. customTo a 25 mL round-bottomed flask equipped with a magnetic stir bar
  2. concentrationThen, the reaction mixture was concentrated de vacuo
  3. custompurified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane)

出典と根拠

ORDレコード
ord-8c050556713441ef80d0300ac5a35769
出典データセット
uspto-grants-2013_02
特許番号
US08367713B2

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