Ethyl 3-aminobenzoate → Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate

HRID 248692

Reaktionsgleichung

Reaktionsgleichung von HRID 248692
[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].[NH2:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([NH:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:9])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 11400Ethyl 3-aminobenzoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic Acid

Produkt 1

HCID 15670143Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoateAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Acetylthiomethyl-3-phenylpropionic acid (11.9 g) and ethyl 3-aminobenzoate (8.26 g) are dissolved in dichloromethane (150 ml), and thereto are added 4-dimethylaminopyridine (0.61 g) and EDC.HCl (10.54 g), and the mixture is stirred at room temperature overnight. The reaction mixture is washed with saturated aqueous citric acid solution, saturated aqueous sodium chloride solution and saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in this order, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is washed with diethyl ether to give the title compound (13 g).

Aufarbeitung

  1. washThe reaction mixture is washed with saturated aqueous citric acid solution, saturated aqueous sodium chloride solution and saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in this order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. washThe residue is washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0523243cb0aa491d8a790635ab59cd54
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210266

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