Reacción #2275720

Ecuación de reacción

[(3-hydroxy-pyridine-2-carbonyl)methylamino]acetic acid ethyl ester

H2O

NaOH

→

desired compound

Rendimiento 85.0%

[(3-hydroxy-pyridine-2-carbonyl)-methyl-amino]-acetic acid

Rendimiento 85.0%

Disolventes

THF

CHCl3 isopropanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthen concentrated under reduced pressure
2. 2
   Concentraciónthe solution is concentrated under reduced pressure
3. 3
   Otroto give an off-white solid
4. 4
   Filtraciónthen collected by filtration
5. 5
   LavadoThe solid is washed with additional CHCl3:isopropanol (1:1)
6. 6
   Otrothen transferred to a flask
7. 7
   Otrotriturated with Et2O

Procedimiento

To a solution of [(3-hydroxy-pyridine-2-carbonyl)methylamino]acetic acid ethyl ester, 32, (0.10 g, 0.42 mmol) in THF (4 mL) is added H2O (1 mL) and NaOH (0.90 g, 2.25 mmol). The reaction is stirred for 3 hours then concentrated under reduced pressure. The remaining oil is acidified to pH ˜1 with 1M HCl and the solution is concentrated under reduced pressure to give an off-white solid. The solid is suspended in CHCl3:isopropanol (1:1) then collected by filtration. The solid is washed with additional CHCl3:isopropanol (1:1) then transferred to a flask and triturated with Et2O to afford 0.075 g (85% yield) of the desired compound as a pale yellow solid. 1H NMR (250 MHz, MeOD) δ ppm (rotamers) 8.26 (1H, br s), 7.63-7.74 (1H, m), 7.56-7.63 (1H, m), 4.38 (1H, s), 4.32 (1H, s), 3.20 (1.5H, s), 3.12 (1.5H, s). HPLC-MS: m/z 211 [M+H]+.

Fuente