Reacción #81180

Ecuación de reacción

chloromethyl pivalate

potassium carbonate

1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid

ethyl acetate

→

title compound

Pivaloyloxymethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

Disolventes

N,N-dimethylacetamide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat 50° C. for 2 hours
2. 2
   OtroThe ethyl acetate layer was separated
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Otroafter which the solvent was removed by distillation under reduced pressure
5. 5
   OtroThe resulting residue was purified by column chromatography through silica gel
6. 6
   workup.ADDITIONby volume mixture of ethyl acetate and hexane as the eluent

Procedimiento

2.13 ml of chloromethyl pivalate and 3.99 g of potassium carbonate were added to a solution of 6 g of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid [prepared as described in step (b) above] in 70 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 1 hour and then at 50° C. for 2 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 6.80 g of the title compound as crystals, melting at 106°-107° C.

Fuente