Hydrochloric Acid → Ethyl 2-amino-2-(4-bromophenyl)propanoate

HRID 79638Notes

Reaction equation

HRID 79638 reaction equation
[NH2:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].Cl.[CH2:15](O)[CH3:16]>>[CH2:15]([O:4][C:3](=[O:5])[C:2]([NH2:1])([C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)[CH3:6])[CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 31587702-Amino-2-(4-bromophenyl)propanoic acid

Product 1

HCID 3494252Ethyl 2-amino-2-(4-bromophenyl)propanoateYield 72%

Procedure

To a solution of 2-amino-2-(4-bromo-phenyl)-propionic acid (1.0 g, 4.1 mmol) in ethanol (20 mL) was bubbled through HCl gas for five minutes. The mixture was stirred at ambient for 24 hours, then refluxed for 18 hours. The volatile component was removed in vacuo, and the residue was dissolved in ethyl acetate (150 mL), washed with NaHCO3 solution, water and brine, dried over MgSO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product (800 mg, 72%). m/z 271.7, 273.7 (M+H)+.

Workup

  1. temperaturerefluxed for 18 hours
  2. customThe volatile component was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (150 mL)
  4. washwashed with NaHCO3 solution, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3e6b9bddb8dc434996304f903164424e
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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