Ethyl Acrylate → Ethyl N-(2-ethoxy-2-oxoethyl)-N-(phenylmethyl)-beta-alaninate

HRID 2415651Notes

Reaction equation

HRID 2415651 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=[CH2:17]>C(Cl)Cl>[CH2:20]([O:19][C:15](=[O:18])[CH2:16][CH2:17][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:21]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 80908N-Benzylglycine ethyl ester

Product 1

HCID 69929Ethyl N-(2-ethoxy-2-oxoethyl)-N-(phenylmethyl)-beta-alaninateYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl N-benzylglycinate (0.1295 mol, 1 eq), ethyl acrylate (0.142 mol, 1.1 eq) and 155 μL of Triton™ B (available from Sigma-Aldrich, St. Louis, Mo.) were combined at room temperature under N2. The mixture was then heated to reflux overnight. An aliquot was removed and NMR spectrum was taken of the crude material. The product was present plus both starting materials. The excess of the ethyl acrylate was removed under vacuum at 10 mmHg (60° C. water bath). The crude amber oil that resulted was dissolved in 50 mL of CH2Cl2 and was charge onto a Biotage™ 75L cartridge and eluted with the following gradient 0.5% by volume acetone in hexanes, 1% (1200 mL), 1.5% (1200 mL) and 2.5% (3600 mL). The fractions containing the desired product were combined and concentrated to a colorless oil which was dried under high vacuum for 2 hours to afford 29 g (76%) of product (I-4a). 1H NMR spectrum (CDCl3) and LC/MS (294) were consistent with the compound I-4a.

Workup

  1. customwere combined at room temperature under N2
  2. temperatureThe mixture was then heated
  3. temperatureto reflux overnight
  4. customAn aliquot was removed
  5. customThe excess of the ethyl acrylate was removed under vacuum at 10 mmHg (60° C. water bath)
  6. customThe crude amber oil that resulted
  7. washeluted with the following gradient 0.5% by volume acetone in hexanes, 1% (1200 mL), 1.5% (1200 mL) and 2.5% (3600 mL)
  8. additionThe fractions containing the desired product
  9. concentrationconcentrated to a colorless oil which
  10. customwas dried under high vacuum for 2 hours

Sources & evidence

ORD record
ord-974ffafd474848b28b3ed18dedd1b8d4
Source dataset
uspto-grants-2004_11
Patent number
US06821964B2

Reaction notes

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