Triethylamine → Ethyl 3-(ethoxycarbonylmethylamino)propionate
Reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11].C(N(CC)CC)C>C(O)C>[CH2:2]([O:4][C:5]([CH2:6][NH:7][CH2:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])=[O:8])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
150 g of glycine ethyl ester hydrochloride (1.07 mol) was mixed with 1.200 L of ethanol. To this mixture, 110 mL of ethyl acrylate (1.02 mol) was added at an internal temperature of 2 to 25° C. 150 mL of triethylamine (1.08 mol) was then added dropwise at an internal temperature of 20 to 21° C. over 5 minutes. Subsequently, the mixture was stirred at an internal temperature of 23 to 27° C. for 8.5 hours and was allowed to stand overnight. The insoluble material was separated by filtration and the filtrate was evaporated under reduced pressure. 300 mL of ethyl acetate was added to the resulting residue and the insoluble material was separated by filtration and washed with 50 mL of ethyl acetate. The filtrate and the wash were combined and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (533 Pa, 130° C.) to give 138 g of the title compound as a colorless oil (67% yield).
Workup
- waitto stand overnight
- customThe insoluble material was separated by filtration
- customthe filtrate was evaporated under reduced pressure
- addition300 mL of ethyl acetate was added to the resulting residue
- customthe insoluble material was separated by filtration
- washwashed with 50 mL of ethyl acetate
- concentrationconcentrated under reduced pressure
- distillationThe resulting residue was distilled under reduced pressure (533 Pa, 130° C.)
Sources & evidence
- ORD record
- ord-bfd9fbc46d3f4af09e398b819123c962
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07667049B2
Reaction notes
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