Triethylamine → Methyl 4-[(2-ethoxy-2-oxoethyl)amino]-4-oxobutanoate

HRID 2389908Notes

Reaction equation

HRID 2389908 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.Cl[C:17](=[O:24])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]>O1CCCC1.O>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:17](=[O:24])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 280754Methyl 4-[(2-ethoxy-2-oxoethyl)amino]-4-oxobutanoateYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of glycine ethyl ester hydrochloride (5.00 g, 35.8 mmol) in tetrahydrofuran (300 mL) were added triethylamine (9.99 mL, 71.6 mmol) and methyl 4-chloro-4-oxobutyrate (5.39 g, 35.8 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by recrystallization (ethyl acetate/hexane) to give the title compound (5.05 g, yield 65%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-aec6249032564afb92c3b20a7258578f
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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