Ethanol → Ethyl 2-amino-2-(4-fluorophenyl)acetate

HRID 475849Notes

Reaction equation

HRID 475849 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].OS(O)(=O)=O.[CH2:18](O)[CH3:19]>>[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([O:5][CH2:18][CH3:19])=[O:4]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 98313(1)-4-Fluorophenylglycine

Product 1

HCID 5178419Ethyl 2-amino-2-(4-fluorophenyl)acetateYield 65%

Procedure

To a cooled solution of 2-amino-2-(4-fluorophenyl)acetic acid (1.0 g, 6.17 mmol) in ethanol was added con. H2SO4 (1 mL) over a period of 1 min. The reaction mixture was heated at reflux for 5 h. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate (20 mL). The organic solution was washed with aqueous saturated NaHCO3 (15 mL×2), water (20 mL), brine solution (10 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to give ethyl 2-amino-2-(4-fluorophenyl)acetate (0.75 g, 65%) as crude compound (oily liquid). The crude compound was taken to the next step without further purification. LC-MS (M+H2O)+=198.0. 1H NMR (400 MHz, DMSO-d6): δ 7.44-7.40 (2H, m), 7.18-7.13 (2H, m), 4.51 (1H, s), 4.12-4.01 (2H, m), 2.26 (2H, s), 1.12 (3H, t, J=8.0 Hz).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate (20 mL)
  5. washThe organic solution was washed with aqueous saturated NaHCO3 (15 mL×2), water (20 mL), brine solution (10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-acfa3a6638514255ac1823facbdf58da
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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