[2-Amino-2-(3-bromo-phenyl)-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester → 5-(3-Bromo-phenyl)-5-trifluoromethyl-morpholin-3-one

HRID 2196239Notes

Reaction equation

HRID 2196239 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][CH2:7][C:8]([NH2:20])([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1)[C:9]([F:12])([F:11])[F:10])C>C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O>[Br:19][C:15]1[CH:14]=[C:13]([C:8]2([C:9]([F:12])([F:11])[F:10])[NH:20][C:4](=[O:3])[CH2:5][O:6][CH2:7]2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 66666183[2-Amino-2-(3-bromo-phenyl)-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester

Product 1

HCID 666654105-(3-Bromo-phenyl)-5-trifluoromethyl-morpholin-3-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 598 mg (1.616 mmol) [2-Amino-2-(3-bromo-phenyl)-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester in 5.4 ml toluene and 2.7 ml TFA was heated at reflux temperature for 5 h. The cooled down mixture was evaporated, taken up in EtOAc, washed with 5% aqueous NaHCO3, dried with Na2SO4 and evaporated to give the essentially pure title compound as a colorless solid.

Workup

  1. temperatureat reflux temperature for 5 h
  2. temperatureThe cooled down mixture
  3. customwas evaporated
  4. washwashed with 5% aqueous NaHCO3
  5. dry with materialdried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-ed03c387fe5a4541a1e20f7831138b3f
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

Loading…