Reacción #2275714

Ecuación de reacción

[(3,5-bis-benzyloxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

→

desired compound

Rendimiento 66.0%

[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

Rendimiento 66.0%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe suspension is then filtered through Celite™
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   Otrothe crude product purified over silica (2.5% MeOH/CH2Cl2)

Procedimiento

A solution of [(3,5-bis-benzyloxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester, 26, (3.04 g, 6.79 mmol) in EtOH (100 mL) containing 10% Pd/C (0.300 g) is stirred under an atmosphere of H2 for 22 hours. The suspension is then filtered through Celite™, concentrated under reduced pressure, and the crude product purified over silica (2.5% MeOH/CH2Cl2) to afford 1.20 g (66% yield) of the desired compound as a colorless oil. 1H NMR (250 MHz, CDCl3) δ ppm 11.90 (1H, br s), 8.94 (1H, br s), 8.20 (1H, t, J=5.6 Hz), 7.76 (1H, d, J=2.4 Hz), 6.77 (1H, d, J=2.1 Hz), 4.13 (2H, d, J=5.5 Hz), 1.53 (9H, s). HPLC-MS: m/z 269 [M+H]+.

Fuente