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Triethylamine → 1-ethyl-1-methylpropyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate

HRID 2061232
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HRID 2061232 반응식
[CH2:1]([C:3]([CH3:14])([O:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])[CH2:4][CH3:5])[CH3:2].[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl.CN(C)C=O>[CH:15]1[C:25]2[CH:24]=[CH:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20](=[C:30]3[CH2:31][CH2:32][N:33]([C:11](=[O:13])[CH2:10][NH:9][C:7](=[O:8])[O:6][C:3]([CH2:1][CH3:2])([CH3:14])[CH2:4][CH3:5])[CH2:34][CH2:35]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1
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참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 85792234{[(1-Ethyl-1-methylpropoxy)carbonyl]amino}acetic acid

생성물 1

HCID 59853919
1-ethyl-1-methylpropyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

284 mg (1.40 mmol) of {[(1-ethyl-1-methylpropoxy)carbonyl]-amino}-acetic acid, 320 mg (1.17 mmol) of 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-piperidine and 322 mg (1.68 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride were dissolved in a mixed solvent of 15 ml of dichloromethane and 5 ml of dimethylformamide. 0.23 ml (1.68 mmol) of triethylamine and 14.7 mg (0.12 mmol) of dimethylaminopyridine were added to the obtained solution, and they were stirred at room temperature overnight. After the concentration under reduced pressure, ethyl acetate was added to the reaction mixture. The resultant mixture was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by the silica gel chromatography (hexane:dichloromethane=95:5 to 2:3) to obtain the title compound.

후처리

  1. concentrationAfter the concentration under reduced pressure, ethyl acetate
  2. additionwas added to the reaction mixture
  3. washThe resultant mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by the silica gel chromatography (hexane:dichloromethane=95:5 to 2:3)

출처 및 근거

ORD 기록
ord-ec38d52018ae45998077107d6402f576
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08278329B2

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