Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 1499382Notes

Reaction equation

HRID 1499382 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 ethyl 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-c5c0bab0331d4629b1eba27c1ca2ac71
Source dataset
uspto-grants-2015_12
Patent number
US09200282B2

Reaction notes

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