Réaction #1509588

ord-621cc250a12749e2ad2a403d76975118

Équation de réaction

COC(=O)c1cc(NC(=O)OC(C)(C)C)cc(C(C)(C)C)c1
Methyl 3-(tert.-butoxycarbonylamino)-5-tert-butylbenzoate
O=C(O)C(F)(F)F
TFA
CCOC(=O)c1cc(N)cc(C(C)(C)C)c1
ethyl 3-amino-5-tert-butylbenzoate

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Concentrationconcentrated in vacuum
  2. 2
    workup.DISSOLUTIONThe residue was dissolved in DCM
  3. 3
    Extractionextracted with aqueous sodium bicarbonate solution
  4. 4
    AutreThe organic layer was separated
  5. 5
    Séchagedried over sodium sulphate
  6. 6
    Concentrationconcentrated in vacuum

Mode opératoire

Methyl 3-(tert.-butoxycarbonylamino)-5-tert-butylbenzoate (0.42 g) was dissolved in DCM (5 ml). To the resulting solution, TFA (1 ml) was added, the mixture was stirred for 30 min at room temperature and then concentrated in vacuum. The residue was dissolved in DCM and extracted with aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulphate and concentrated in vacuum to yield ethyl 3-amino-5-tert-butylbenzoate (0.28 g), which was used for the synthesis of example 112 without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE045323E1uspto-grants-2015_01