Reacción #362000

Ecuación de reacción

5-methoxycarbonyl-4-hydroxy-methyl-2-propyl-1-[(2'-(N-trityltetrazol-5-yl)biphen-4-yl)methyl]imidazole

ethyl acetate

→

title compound

Rendimiento 81.0%

5-Methoxycarbonyl-2-propyl-1-[(2'-(N-trityltetrazol-5-yl)biphen-4-yl)methyl]imidazol-4-carboxaldehyde

Rendimiento 81.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe product was filtered through Celite™
2. 2
   Lavadothe cake was washed with ethyl acetate and methylene chloride
3. 3
   Otrothe filtrate was evaporated under reduced pressure

Procedimiento

A suspension of 10.00 g (14.82 mmole) of 5-methoxycarbonyl-4-hydroxy-methyl-2-propyl-1-[(2'-(N-trityltetrazol-5-yl)biphen-4-yl)methyl]imidazole (Example 101, Part A) in 200 mL THF was added to a stirring slurry of 12.88 g (148.2 mmole) of MnO2 at room temperature. The mixture was stirred at room temperature for 2 days. 3.22 g (37.0 mmole) of additional MnO2 was added to the mixture and stirred at room temperature for 5 hours after which TLC (ethyl acetate) showed no starting material. The product was filtered through Celite™, and the cake was washed with ethyl acetate and methylene chloride; the filtrate was evaporated under reduced pressure to give 8.10 g (81%) of the title compound as a light-yellow-colored solid. 1H NMR (300 MHz, CDCl3): δ 0.89 (t, J=7.3 Hz, 3H); 1.74 (m, 2H); 2.58 (t, J=7.7 Hz, 2H); 3.81 (s 3H); 5.49 (s, 2H); 6.74-7.92 (m, 23H); 10.38 (s, 1H). MS (NH3 -DCI): m/z 673 (M+H, 10%); 617 (M+H--N44, 100 %); 243 (Tr, 20%). Calculated mass for C42H37N6O3 (M+H): 673.292714; found: 673.292470.

Fuente