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

HRID 1607397노트

반응식

HRID 1607397 반응식
[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]

참가 물질

5

반응물 3

HCID 1150TryptamineHCID 682631,1'-CarbonyldiimidazoleHCID 19790805HCID 19790805, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-31b381b0090e4a35a51c3f6a9acb9a65
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863904

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