Water → 4-(((6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl)oxy)-N,N-dimethylbutan-1-amine

HRID 530168

반응식

HRID 530168 반응식
CS([O:5][CH:6]([CH:17]([CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=O)=O.[CH3:38][N:39]([CH:41](O)[CH2:42][CH2:43][CH3:44])[CH3:40].[H-].[Na+].O>C1(C)C=CC=CC=1>[CH2:18]([CH:17]([CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:6]([O:5][CH2:44][CH2:43][CH2:42][CH2:41][N:39]([CH3:40])[CH3:38])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 19917359DimethylaminobutanolHCID 89775026(6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl methanesulfonate

생성물 1

HCID 897750254-(((6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl)oxy)-N,N-dimethylbutan-1-amine수율 13%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
115 °C

실험 절차

A solution of the mesylate 61 (1.09 g, 2.01 mmol) in toluene (30 mL) was successively treated with N,N-dimethylaminobutanol (1.34 mL, 10.1 mmol) and NaH (442 mg as a 60% dispersion in oil, 11.1 mmol). Once gas evolution ceased the reaction mixture was brought to reflux (115° C. bath temp.) and stirred (50 h). The reaction mixture was then cooled (rt) and poured into cold water and then extracted with EtOAc. The combined organics were washed with water and brine, dried (Na2SO4), filtered, concentrated and purified via chromatography (100% EtOAc) to yield 4-(((6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl)oxy)-N,N-dimethylbutan-1-amine 62 (143 mg, 13%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 5.41-5.30 (m, 6H), 3.46-3.35 (m, 2H), 3.19-3.14 (m, 1H), 2.34 (t, 2H), 2.24 (s, 6H), 2.10-1.93 (m, 12H), 1.60-1.09 (m, 35H), 0.90 (t, 9H). Rf 0.54 (10% MeOH—CH2Cl2).

후처리

  1. temperatureThe reaction mixture was then cooled (rt)
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via chromatography (100% EtOAc)

출처 및 근거

ORD 기록
ord-c62e33e72ac2448e9788be9f9f331d43
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09352042B2

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