Triethylamine → N-(2-azidoethyl)tetradecanamide

HRID 384186

반응식

HRID 384186 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 57914356N-(2-azidoethyl)tetradecanamide수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8c050556713441ef80d0300ac5a35769
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367713B2

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