Reacción #2275700

Ecuación de reacción

HCl

{[5-(3-chloro-phenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}-acetic acid methyl ester

NaOH

→

desired product

Rendimiento 64.0%

{[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}-acetic acid

Rendimiento 64.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent removed under reduced pressure
2. 2
   Filtraciónfiltered
3. 3
   Secadothe filtrate dried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónre-concentrated under reduced pressure
6. 6
   OtroThe crude material is triturated with a small amount of MeOH

Procedimiento

To a solution of {[5-(3-chloro-phenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}-acetic acid methyl ester, 6, (0.163 g, 0.509 mmol) in THF (5 mL) is added 1M NaOH (1.5 ml, 1.27 mmol) and the reaction mixture stirred at room temperature for 1 hour. The solution is acidified using 1M HCl (3 mL), the solvent removed under reduced pressure and the resulting solid suspended in CHCl3:iso-propanol (1:1), filtered and the filtrate dried (MgSO4), filtered and re-concentrated under reduced pressure. The crude material is triturated with a small amount of MeOH to afford 0.10 g (64% yield) of the desired product as a colorless solid. 1H NMR (400 MHz, MeOD) δ ppm 8.31 (1H, d, J=1.8 Hz), 7.47 (2H, d, J=1.8 Hz), 7.30-7.65 (4H, m), 4.07 (2H, s). HPLC-MS: m/z 307 [M+H]+.

Fuente