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Diethyl Ether → Tert-butyl 2-{[2-(tritylamino)ethyl]amino}ethylcarbamate

HRID 459608
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인쇄 미리보기

반응식

HRID 459608 반응식
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:19][CH2:20][NH:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)C>C(Cl)(Cl)Cl.CCCCCC>[C:22]([NH:21][CH2:20][CH2:19][NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 187201N-BOC-ethylenediamineHCID 15718287(2-Bromoethyl)tritylamine

생성물 1

HCID 18442413Tert-butyl 2-{[2-(tritylamino)ethyl]amino}ethylcarbamate수율 41.8%

시약·촉매·용매 2

HCID 6212
Chloroform
용매
HCID 8058Hexane용매

실험 절차

To a solution of tert-butyl 2-aminoethylcarbamate (4.81 g) in dehydrated chloroform (10 ml) were added sodium carbonate (1.06 g) and N-(2-bromoethyl)tritylamine (3.66 g), and the mixture was stirred under reflux for 3 hours. To the reaction mixture were added diethyl ether and hexane, and the solution was washed with water. The mixture was extracted with 5% aqueous citric acid solution, and the aqueous layer was washed with diethyl ether. The aqueous layer was then made alkaline with sodium hydrogencarbonate followed by extraction with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give tert-butyl 2-{[2-(tritylamino)ethyl]amino}ethylcarbamate (1.86 g) as a viscous oil.

후처리

  1. temperatureunder reflux for 3 hours
  2. washthe solution was washed with water
  3. extractionThe mixture was extracted with 5% aqueous citric acid solution
  4. washthe aqueous layer was washed with diethyl ether
  5. extractionfollowed by extraction with diethyl ether
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f7d27343a9094619b1ae392f183741ec
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07192943B2

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