Reaction #70334

Reaction equation

methyl 2-(6-(benzyloxy)-5-phenylpyridin-3-ylamino)-5-cyclopropylbenzoate

→

5-Cyclopropyl-2-(6-hydroxy-5-phenylpyridin-3-ylamino)benzoic acid

Solvents

TFA

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.ADDITION2N aqueous NaOH were added
3. 3
   OtherThe solvent was removed
4. 4
   Extractionextracted with CHCl3
5. 5
   OtherThe crude mixture was purified by ionic exchange through a SCX cartridge
6. 6
   Otheraffording
7. 7
   Other0.060 g (50% of yield)

Procedure

A solution of methyl 2-(6-(benzyloxy)-5-phenylpyridin-3-ylamino)-5-cyclopropylbenzoate (0.34 mmol, 0.155 g) in TFA (1.3 ml) was stirred at 45° C. for 30 minutes. The solvent was removed under reduced pressure. The crude mixture was solved in ethanol (2 ml), 2N aqueous NaOH were added and stirred at room temperature for 16 hours. The solvent was removed and the crude was neutralised with 2N aqueous HCl and extracted with CHCl3. The crude mixture was purified by ionic exchange through a SCX cartridge affording 0.060 g (50% of yield).

Source