Reaction #2275712

Reaction equation

HCl

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

H2O

LiOH.H2O

→

desired compound

Yield 12.0%

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

Yield 12.0%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe solvents are removed under reduced pressure
2. 2
   workup.ADDITIONthe solid that remains is suspended in a mixture of THF
3. 3
   FiltrationMeOH and filtered
4. 4
   ConcentrationThe filtrate is concentrated under reduced pressure
5. 5
   Otherthe resulting solid is triturated with MeOH
6. 6
   Filtrationcollected by filtration

Procedure

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]+.

Source