Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 386751Notes

Reaction equation

HRID 386751 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[OH-].[Na+].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13]>O>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][NH:2][CH2:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])[CH3:8]

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

To ethyl glycinate hydrochloride (12.9 g, 92 mmol) in water (20 mL) at 0° C. was added cold aqueous NaOH (19.5 mL, 93 mmol, 4.75 M) followed by ethyl acrylate (9.18 g, 92 mmol). The reaction stirred about 18 hours and warmed to room temperature. The mixture was extracted with CH2Cl2 four times and the solution was dried (Na2SO4). The material was distilled at about 110° C. (1.8 torr) to afford the product, 1-a.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 four times
  2. dry with materialthe solution was dried (Na2SO4)
  3. distillationThe material was distilled at about 110° C. (1.8 torr)

Sources & evidence

ORD record
ord-ba616bac689949279fd8846f549a690c
Source dataset
uspto-grants-2013_02
Patent number
US08372863B2

Reaction notes

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