Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 1404466Notes

Reaction equation

HRID 1404466 reaction equation
[OH-].[Na+].Cl.[NH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13]>O>[CH2:9]([O:8][C:6]([CH2:5][NH:4][CH2:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 14798Sodium HydroxideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 281012Ethyl 3-(ethoxycarbonylmethylamino)propionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 4.7 M aqueous solution of sodium hydroxide (50 mL) is added into a stirred, ice-cooled solution of ethyl glycinate hydrochloride (32.19 g, 0.23 mole) in water (50 mL). Then, ethyl acrylate (23.1 g, 0.23 mole) is added and the mixture is stirred at room temperature until completion of the reaction is ascertained by TLC. After 19 h the solution is partitioned with dichloromethane (3×100 mL). The organic layer is dried with anhydrous sodium sulfate, filtered and evaporated. The residue is distilled to afford AA (28.8 g, 61%).

Workup

  1. customAfter 19 h the solution is partitioned with dichloromethane (3×100 mL)
  2. dry with materialThe organic layer is dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. distillationThe residue is distilled
  6. customto afford AA (28.8 g, 61%)

Sources & evidence

ORD record
ord-4c2105f5abbe4b30b34dacdb4c7b477e
Source dataset
uspto-grants-2014_12
Patent number
US08912316B2

Reaction notes

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