Reacción #9786

Ecuación de reacción

2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile

intermediate 101

2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile

hydrochloric acid

→

(4-{2-[5-(4-cyano-3-fluorophenyl)-3-methylthien-2-yl]ethyl}-2-methylphenoxy)acetic acid

Disolventes

2-propanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 2 hours
2. 2
   OtroThe solvent was removed
3. 3
   workup.DISSOLUTIONthe residue dissolved in 1,4-dioxane (2 ml)
4. 4
   workup.ADDITIONThis mixture was treated with 2M aqueous sodium hydroxide (0.5 ml)
5. 5
   workup.STIRRINGthe mixture stirred for 16 hours)
6. 6
   OtroThe solvent was removed
7. 7
   Otrothe residue purified by SPE (aminopropyl)
8. 8
   OtroThe title compound, as the free acid, was recovered
9. 9
   workup.ADDITIONby treating a solution of this product with Dowex H+

Procedimiento

A mixture of 2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile (intermediate 101, 0.016 g) in 2-propanol (2 ml) was treated with 2M aqueous hydrochloric acid (1 ml) and the mixture stirred at reflux for 2 hours. The solvent was removed and the residue dissolved in 1,4-dioxane (2 ml) and water (1 ml). This mixture was treated with 2M aqueous sodium hydroxide (0.5 ml) and the mixture stirred for 16 hours). The solvent was removed and the residue purified by SPE (aminopropyl). The title compound, as the free acid, was recovered by treating a solution of this product with Dowex H+.

Fuente