Beta-Alanine → N-(2-Carboxyethyl)-β-alanine 1-(phenylmethyl) ester

HRID 2369793Notes

Reaction equation

HRID 2369793 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].O.[CH2:8]([O:15][C:16](=[O:19])[CH:17]=[CH2:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[CH2:8]([O:15][C:16]([CH2:17][CH2:18][NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 962WaterHCID 75617Benzyl acrylate

Product 1

HCID 68733661N-(2-Carboxyethyl)-β-alanine 1-(phenylmethyl) ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Aminopropionic acid (5 g, 56 mmol) was added to ethanol (50 mL), and TEA (7.8 ml, 56 mmol) and water (50 mL) were added and the mixture was refluxed under nitrogen. Acrylic acid benzyl ester ((9.1 g, 56 mmol) and more ethanol (50 mL) were added, and the mixture was refluxed for 16 h. The sample was concentrated under vacuum, adding toluene and reevaporating twice to yield 17.5 grams (product plus TEA).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed under nitrogen
  3. temperaturethe mixture was refluxed for 16 h
  4. concentrationThe sample was concentrated under vacuum
  5. additionadding toluene
  6. customreevaporating twice
  7. customto yield 17.5 grams (product plus TEA)

Sources & evidence

ORD record
ord-a6b158e607894b47b464fb716a442ea4
Source dataset
uspto-grants-2014_04
Patent number
US08710000B2

Reaction notes

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