Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 20909Notes

Reaction equation

HRID 20909 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>[CH2:16]([O:15][C:11](=[O:14])[CH2:12][CH2:13][NH:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:17]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 14798Sodium HydroxideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 281012Ethyl 3-(ethoxycarbonylmethylamino)propionateYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Referring to scheme 16, a 4.7M 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 the completion of reaction was ascertained by TLC (19 h). After 19 h which it 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 58 (28.8 g, 61%).

Workup

  1. customwas ascertained by TLC (19 h)
  2. customAfter 19 h which it was partitioned with dichloromethane (3×100 mL)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-83d523f1f3ab4c6cb52549770aa930ad
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Reaction notes

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