Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 2237383Notes

Reaction equation

HRID 2237383 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) was added into a stirred, ice-cooled solution of ehtyl glycinate hydrochloride (32.19 g, 0.23 mole) in water (50 mL). Then, ethyl acrylate (23.1 g, 0.23 mole) was added and the mixture was stirred at room temperature until completion of the reaction was ascertained by TLC. After 19 h the solution was partitioned with dichloromethane (3×100 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and evaporated. The residue was distilled to afford AA (28.8 g, 61%).

Workup

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

Sources & evidence

ORD record
ord-4714448328554c1b9de1769a90026605
Source dataset
uspto-grants-2010_05
Patent number
US07718629B2

Reaction notes

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