Réaction #81268

Équation de réaction

water

potassium t-butoxide

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

methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate

→

title compound

Rendement 76.5%

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

Rendement 76.5%

Solvants

N,N-dimethylacetamide

N,N-dimethylacetamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was first stirred at room temperature for 4 hours
2. 2
   workup.WAITat 50° C. for a further 2 hours
3. 3
   Extractionextracted with ethyl acetate
4. 4
   SéchageThe extract was dried over anhydrous magnesium sulfate
5. 5
   Autrethe solvent was removed by distillation under reduced pressure
6. 6
   AutreThe resulting residue was purified by column chromatography through silica gel
7. 7
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

Mode opératoire

194 mg of potassium t-butoxide were added, whilst ice-cooling, to a solution of 359 mg of methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate [prepared as described in Preparation 42(v)] in 5 ml of N,N-dimethylacetamide, and the resulting mixture was stirred for 15 minutes. An the end of this time, a solution of 1.32 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 10 ml of N,N-dimethylacetamide was added. The mixture was first stirred at room temperature for 4 hours and then at 50° C. for a further 2 hours. The reaction mixture was then mixed with water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 848 mg of the title compound as crystals, melting at 120°-137° C. (with decomposition).

Source