Ethyl Acrylate → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 716570Notes

Reaction equation

HRID 716570 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 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 AA (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
  7. customto afford AA (28.8 g, 61%)

Sources & evidence

ORD record
ord-9795a03ae372441fa029baa7d15036d9
Source dataset
uspto-grants-2015_11
Patent number
US09187747B2

Reaction notes

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