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

HRID 248692

反応式

HRID 248692 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 15670143Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate収率 67.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0523243cb0aa491d8a790635ab59cd54
出典データセット
uspto-grants-1993_05
特許番号
US05210266

関連ノート

読み込み中…