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

HRID 424627Notes

Reaction equation

HRID 424627 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5]Br)[CH3:2].[CH:8]1([NH2:11])[CH2:10][CH2:9]1>CCO>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][NH:11][CH:8]1[CH2:10][CH2:9]1)[CH3:2]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 69828Cyclopropylamine

Product 1

HCID 22476174Glycine, N-cyclopropyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromoacetic acid ethyl ester (14.2 g, 9.37 ml, 84.8 mmol) was added dropwise to a soln. of cyclopropylamine (19.4 g; 23.5 ml, 0.34 mol) in EtOH (100 ml), while cooling with ice. The reaction mixture was stirred at RT for 18 h and then concentrated i. vac. Water was added to the residue and the mixture was extracted with CHCl3 (5×100 ml). The combined organic phases were washed with half-saturated sodium chloride soln., dried with Na2SO4 and concentrated i. vac. The crude product was distilled at approx. 85° C. under 24 mbar. Yield: 12.03 g (99%)

Workup

  1. concentrationconcentrated i
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with CHCl3 (5×100 ml)
  4. washThe combined organic phases were washed with half-saturated sodium chloride soln
  5. dry with material, dried with Na2SO4
  6. concentrationconcentrated i
  7. distillationThe crude product was distilled at approx. 85° C. under 24 mbar

Sources & evidence

ORD record
ord-f983eb0c65494a5385cf3bb50053b669
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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