Reacción #81273

Ecuación de reacción

potassium t-butoxide

4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide

ethyl 2-ethoxyethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate

ethyl acetate

→

title compound

Rendimiento 98.4%

Ethyl 2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Rendimiento 98.4%

Disolventes

N,N-dimethylacetamide

N,N-dimethylacetamide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
2. 2
   workup.STIRRINGshaken
3. 3
   OtroThe ethyl acetate layer was separated
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   OtroThe solvent was removed by distillation under reduced pressure
6. 6
   Otrothe resulting residue was purified by column chromatography through silica gel
7. 7
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

Procedimiento

217 mg of potassium t-butoxide were added, whilst ice-cooling, to a solution of 450 mg of ethyl 2-ethoxyethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate [prepared as described in Preparation 44(iii)] in 5 ml of N,N-dimethylacetamide, and the mixture was stirred for 30 minutes. At the end of this time, a solution of 1.47 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 10 ml of N,N-dimethylacetamide was added dropwise to the mixture. The mixture was stirred at room temperature for 2 hours, after which it was mixed with ethyl acetate and water and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.2 g of the title compound as an amorphous powder.

Fuente