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

HRID 1607397Notes

Reaction equation

HRID 1607397 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-31b381b0090e4a35a51c3f6a9acb9a65
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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