Methyl 2-((tert-butoxycarbonyl)amino)-5-(trifluoromethyl)benzoate → Methyl 2-amino-5-(trifluoromethyl)benzoate

HRID 1279613Notes

Reaction equation

HRID 1279613 reaction equation
C(OC([NH:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 22672049Methyl 2-((tert-butoxycarbonyl)amino)-5-(trifluoromethyl)benzoate

Product 1

HCID 14233808Methyl 2-amino-5-(trifluoromethyl)benzoateYield 90.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of methyl 2-t-butoxycarbonylamino-5-trifluoromethylbenzoate (3.80 g; prepared in Reference Example 27.) in methylene chloride (30 ml), trifluoroacetic acid (6 ml) was added. The mixture was stirred for 8 hours at room temperature. The solvent was distilled off azeotropically with toluene three times. To the reaction mixture, an aqueous sodium hydrogencarbonate solution was added to neutralize. The mixture was extracted with ethyl acetate, washed, dried, filtered and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt 5:1) to give the title compound (2.35 g) having the following physical data.

Workup

  1. distillationThe solvent was distilled off azeotropically with toluene three times
  2. additionTo the reaction mixture, an aqueous sodium hydrogencarbonate solution was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under the reduced pressure
  8. customThe residue was purified on silica gel column chromatography (hexane:AcOEt 5:1)

Sources & evidence

ORD record
ord-a2bd2d08473844abbff0505ca8e6035d
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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