Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 1502513Notes

Reaction equation

HRID 1502513 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-4c07c34c9a624ba0b962b79ee0a9414f
Source dataset
uspto-grants-2015_12
Patent number
US09206421B2

Reaction notes

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