Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 572906Notes

Reaction equation

HRID 572906 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) can be 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) can be added and the mixture can be stirred at room temperature until completion of the reaction can be ascertained by TLC. After 19 h the solution can be partitioned with dichloromethane (3×100 mL). The organic layer can be dried with anhydrous sodium sulfate, filtered and evaporated. The residue can be distilled to afford AA (28.8 g, 61%).

Workup

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

Sources & evidence

ORD record
ord-fcaa26b82daf4e49bb3d638ccfbdd727
Source dataset
uspto-grants-2015_05
Patent number
US09029525B2

Reaction notes

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