Reaction #1509588

Reaction equation

Methyl 3-(tert.-butoxycarbonylamino)-5-tert-butylbenzoate

TFA

→

ethyl 3-amino-5-tert-butylbenzoate

Solvents

DCM

Conditions

Workup

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

Procedure

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