Ethyl Acrylate → N-(3-Methoxy-2-methyl-3-oxopropyl)-N-(phenylmethyl)-beta-alanine ethyl ester

HRID 2165112Notes

Reaction equation

HRID 2165112 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH3:14])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH2:18]>CO>[CH3:1][O:2][C:3]([CH:4]([CH3:14])[CH2:5][N:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:18][CH2:17][C:16]([O:20][CH2:21][CH3:22])=[O:19])=[O:15]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 97781Methyl 2-methyl-3-[(phenylmethyl)amino]propanoate

Product 1

HCID 98098N-(3-Methoxy-2-methyl-3-oxopropyl)-N-(phenylmethyl)-beta-alanine ethyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Phenylmethylamino-2-methyl-propanoic acid methyl ester (79 g, 0.38 mole) from Example and ethyl acrylate (54.2 ml, 50.06 g, 0.5 mole) were dissolved in 200 ml of methanol and then heated to reflux overnight. After being cooled, the solution was concentrated under vacuum to remove the excess of solvent and ethyl acrylate to yield the crude N-[2-(methoxycarbonyl)propyl]-N-[2-(ethoxycarbonyl)ethyl]phenylmethylamine (110 g, 95%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureAfter being cooled
  4. concentrationthe solution was concentrated under vacuum
  5. customto remove the excess of solvent and ethyl acrylate

Sources & evidence

ORD record
ord-71f8e7accec348169f1cfd8323f4d80d
Source dataset
uspto-grants-1990_07
Patent number
US04939161

Reaction notes

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