Ethyl Acrylate → HCID 18976166, compound

HRID 2393593Notes

Reaction equation

HRID 2393593 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:15][CH:16]1[C:24]2[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=2)[N:18]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:17]1=[O:32]>CS(C)=O>[NH2:15][C:16]1([CH2:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[C:24]2[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=2)[N:18]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:17]1=[O:32]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 11430Potassium CarbonateHCID 18976198HCID 18976198, compound

Product 1

HCID 18976166HCID 18976166, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under argon atmosphere, 0.85 ml of ethyl acrylate and 1.94 g of potassium carbonate were added to 2.00 g of 3-amino-2,3-dihydro-6-methoxy-2-oxo-1-pentyl-1H-indole hydrochloride dissolved in 40 ml of dimethyl sulfoxide, the mixture was stirred at room temperature for 3 hours. The reaction mixture was extracted with ethyl acetate, and the extract was washed and dried. Insolubles were removed by filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography [chloroform-ethyl acetate (1:1)] to afford 1.36 g of ethyl 3-[3-amino-2,3-dihydro-6-methoxy-2-oxo-1-pentyl-1H-indol-3-yl]-propionate as a pale yellow oily product.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed
  3. customdried
  4. customInsolubles were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography [chloroform-ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-b58ebc97553f46fe8ded56d49ce1b8e2
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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