Ethyl bromoacetate → Glycine, N-cyclopropyl-, ethyl ester

HRID 1517360Notes

Reaction equation

HRID 1517360 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:8]1([NH2:11])[CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:8]1([NH:11][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 69828Cyclopropylamine

Product 1

HCID 22476174Glycine, N-cyclopropyl-, ethyl esterYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl bromoacetate (1 eq.) was added slowly to an ice-cold mixture of cyclopropylamine (17.5 mmol, 3 eq.) and K2CO3 (2 eq.) in DMF (25 ml) and the reaction mixture was then stirred at room temperature for 16 h. For working up, the mixture was diluted with water and extracted with 20% ethyl acetate/hexane solution. The organic phase was washed with water and sat. NaCl solution and dried over Na2SO4. After the solvent had been removed completely, the crude product was employed in the next stage without further purification. Yield: 52%

Workup

  1. extractionextracted with 20% ethyl acetate/hexane solution
  2. washThe organic phase was washed with water and sat. NaCl solution
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent had been removed completely
  5. customthe crude product was employed in the next stage without further purification

Sources & evidence

ORD record
ord-ce06ea8ea1de4ba48d0614be27781f3a
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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