Tryptamine → 3-[2-(3-Indolyl)ethylcarbamoyl]-2-(1-naphthylmethyl)propionic acid ethyl ester

HRID 1607397ノート

反応式

HRID 1607397 の反応式
[CH2:1]([O:3][C:4]([CH:6]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[CH2:7][C:8](O)=[O:9])=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:34][CH2:35][CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1>ClCCl>[CH2:1]([O:3][C:4](=[O:5])[CH:6]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[CH2:7][C:8](=[O:9])[NH:34][CH2:35][CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)[CH3:2]

参加物

5

反応物 3

HCID 1150TryptamineHCID 682631,1'-CarbonyldiimidazoleHCID 19790805HCID 19790805、化合物

生成物 1

HCID 539115163-[2-(3-Indolyl)ethylcarbamoyl]-2-(1-naphthylmethyl)propionic acid ethyl ester収率 65%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1.45 g of the butyric acid obtained in 30 ml of dichloromethane was added 0.86 g of 1,1'-carbonyldiimidazole. The mixture was stirred for 1 hour at room temperature. Then, 0.82 g of triptamine was added to the reaction mixture, and the mixture was stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed successively with water, diluted hydrochloric acid and water, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate/benzene=1/1 by volume) to obtain 1.41 g of 3-[2-(3-indolyl)ethylcarbamoyl]-2-(1-naphthylmethyl)propionic acid ethyl ester as a light brown powder.

後処理

  1. stirringthe mixture was stirred for 1.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona 5% aqueous sodium bicarbonate solution was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water, diluted hydrochloric acid and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate/benzene=1/1 by volume)

出典と根拠

ORDレコード
ord-31b381b0090e4a35a51c3f6a9acb9a65
出典データセット
uspto-grants-1989_09
特許番号
US04863904

反応ノート

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