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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 4-(2-{bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amino}-2-oxoethyl)-1-piperidine carboxylate

HRID 68650
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HRID 68650 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][Si:19]([CH3:46])([CH3:45])[CH2:20][CH2:21][O:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH2:29][NH:30][CH2:31][C:32]1[N:33]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:34]=[CH:35][N:36]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.CN(C)C1C=CN=CC=1.O>[CH3:18][Si:19]([CH3:46])([CH3:45])[CH2:20][CH2:21][O:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH2:29][N:30]([CH2:31][C:32]1[N:33]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:34]=[CH:35][N:36]=1)[C:15](=[O:17])[CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1
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참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 67162798N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amine

생성물 1

HCID 67162853tert-butyl 4-(2-{bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amino}-2-oxoethyl)-1-piperidine carboxylate
수율 15.9%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Under an argon atmosphere at room temperature, [1-(tert-butoxycarbonyl)-4-piperidinyl]acetic acid (500 mg) and the compound 2 (899 mg) were dissolved in anhydrous dimethyl formamide (12 mL), and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (590 mg), 1-hydroxybenztriazole (417 mg) and 4-dimethylaminopyridine (377 mg) were added, followed by stirring at room temperature for 16 hours. After the addition of city water and stirring, the obtained solution was extracted three times with ethyl acetate. The organic layer was collected and then washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain the title compound (216 mg) having the following physical properties.

후처리

  1. stirringstirring
  2. extractionthe obtained solution was extracted three times with ethyl acetate
  3. customThe organic layer was collected
  4. washwashed with saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1a918d66fcb246d69898a6bf8353ac98
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822459B2

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