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Diethyl Ether → Tert-butyl 2-{[3-(tritylamino)propyl]amino}ethylcarbamate

HRID 459610
ノート
印刷プレビュー

反応式

HRID 459610 の反応式
[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][CH2:21][NH:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)C>C(Cl)(Cl)Cl.CCCCCC>[C:23]([NH:22][CH2:21][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:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 187201N-BOC-ethylenediamineHCID 2565813-Bromo-N-trityl-1-propanamine

生成物 1

HCID 18442414Tert-butyl 2-{[3-(tritylamino)propyl]amino}ethylcarbamate収率 48.9%

試薬・触媒・溶媒 2

HCID 6212
Chloroform
溶媒
HCID 8058Hexane溶媒

実験手順

To a solution of tert-butyl 2-aminoethylcarbamate (481 mg) in dehydrated chloroform (3 ml) were added sodium carbonate (212 mg) and (3-bromopropyl)tritylamine (694 mg), and the mixture was stirred under reflux for 3.5 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 solution 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-{[3-(tritylamino)propyl]amino}ethylcarbamate (410 mg) as a viscous oil.

後処理

  1. temperatureunder reflux for 3.5 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

出典と根拠

ORDレコード
ord-2afd5841b354430abede72ecd53f0f14
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07192943B2

反応ノート

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