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

HRID 618152Notes

Reaction equation

HRID 618152 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Br[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(Cl)Cl>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][NH:4][CH:1]1[CH2:3][CH2:2]1)[CH3:11]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 69828Cyclopropylamine

Product 1

HCID 22476174Glycine, N-cyclopropyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopropylamine (12.1 mL, 175 mmol) and TEA (42 mL, 385 mmol) were combined at 0° C. in 350 mL CH2Cl2, then ethyl bromoacetate (19.4 mL, 175 mmol) was added dropwise. The reaction was warmed to RT for 3 h, then diluted with additional CH2Cl2, washed with water, sat. NaHCO3, and brine, dried (Na2SO4), filtered and concentrated. Flash filtration (silica, 30% EtOAc/hexane) provided 7-2 as a light yellow oil.

Workup

  1. washwashed with water, sat. NaHCO3, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationFlash filtration (silica, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-be7779995e93436b865703de933e95b0
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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