4-Nitrophenol → 3-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester

HRID 1976886노트

반응식

HRID 1976886 반응식
C(N[C:10](=[O:25])[C:11]([CH3:24])=[CH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=1[NH2:23])CC1C=CC=CC=1.NC1C=C(OC)C(OC)=CC=1C=C(C)C(O)=O.[CH:43]1[C:48]([N+:49]([O-:51])=[O:50])=[CH:47][CH:46]=[C:45]([OH:52])[CH:44]=1.CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C>CCCCCC.C(OCC)(=O)C.ClCCl>[N+:49]([C:48]1[CH:43]=[CH:44][C:45]([O:52][C:10](=[O:25])[C:11]([CH3:24])=[CH:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=2[NH2:23])=[CH:46][CH:47]=1)([O-:51])=[O:50]

참가 물질

8

반응물 5

HCID 9804-NitrophenolHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 702148893-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid phenethyl amideHCID 702156293-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid

생성물 1

HCID 702156313-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester수율 12%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

실험 절차

Into 20 ml of dichloromethane, 0.82 g (3.5 mmol) of (E) 3-(2-amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid and 0.97 g (7 mmol) of p-nitrophenol (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved, and 40 mg of dimethylaminopyridine (manufactured by Wako Pure Chemical Industries, Ltd.) were added thereto. While this mixture was stirred under cooling with ice, 0.81 g (4.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC/HCl) (manufactured by Wako Pure Chemical Industries, Ltd.) were added thereto in portions. The mixture was returned to room temperature and then was stirred for 20 hours. After the end point of the reaction was verified by TLC, the reaction liquid was concentrated under a reduced pressure and then was dissolved in 100 ml of ethyl acetate. After this solution was washed and dried, the solvent was evaporated, whereby a syrupy crude product was obtained. This product was refined by a silica gel column chromatography (n-hexane/ethyl acetate=2/1), whereby 0.15 g of the aimed compound was obtained as a yellow crystal (yield: 12%).

후처리

  1. additionwere added
  2. customwas returned to room temperature
  3. stirringwas stirred for 20 hours
  4. customthe reaction liquid
  5. concentrationwas concentrated under a reduced pressure
  6. dissolutionwas dissolved in 100 ml of ethyl acetate
  7. washAfter this solution was washed
  8. customdried
  9. customthe solvent was evaporated
  10. customwhereby a syrupy crude product was obtained

출처 및 근거

ORD 기록
ord-10ee123fb56f4a1d9165f6e60556c631
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06229020B1

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