Reacción #2275712

Ecuación de reacción

HCl

[(4-(4-methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid methyl ester

H2O

LiOH.H2O

→

desired compound

Rendimiento 12.0%

[(4-(4-Methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid

Rendimiento 12.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvents are removed under reduced pressure
2. 2
   workup.ADDITIONthe solid that remains is suspended in a mixture of THF
3. 3
   FiltraciónMeOH and filtered
4. 4
   ConcentraciónThe filtrate is concentrated under reduced pressure
5. 5
   Otrothe resulting solid is triturated with MeOH
6. 6
   Filtracióncollected by filtration

Procedimiento

To a solution of [(4-(4-methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid methyl ester, 24, (0.092 g, 0.32 mmol) in THF (2 mL) at room temperature is added H2O (1 mL) and LiOH.H2O (0.027 g, 0.64 mmol). The reaction is stirred for 16 hours after which time the solution is acidified using 1M HCl. The solvents are removed under reduced pressure and the solid that remains is suspended in a mixture of THF: MeOH and filtered. The filtrate is concentrated under reduced pressure and the resulting solid is triturated with MeOH and collected by filtration to provide 0.012 g (12% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, MeOD) δ ppm 8.69 (1H, d, J=4.8 Hz), 8.38 (1H, s), 7.86 (1H, d, J=6.2 Hz), 7.72 (2H, d, J=8.1 Hz), 7.38 (1H, d, J=7.9 Hz), 4.21 (1H, s), 2.44 (2H, s). HPLC-MS: m/z 271 [M+H]+.

Fuente