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

HRID 1006548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006548
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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 14233808Methyl 2-amino-5-(trifluoromethyl)benzoateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-t-butoxycarbonylamino-5-trifluoromethyl-benzoate (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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2201400c0afb4743a696202279d40f7f
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790866B2

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