Reacción #47622

Ecuación de reacción

lithium hydroxide monohydrate

3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester

tetrahydrofuran

→

3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid

Rendimiento 74.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter such time, the mixture was concentrated in vacuo
2. 2
   Otroto remove the tetrahydrofuran
3. 3
   workup.ADDITIONdiluted with 1N aqueous hydrochloric acid until the pH
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   SecadoThe organic layers were dried over sodium sulfate
6. 6
   Concentraciónconcentrated in vacuo

Procedimiento

A mixture of 3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (56 mg, 0.13 mmol) in a 1:1 solution of tetrahydrofuran:water (4 mL) was treated with lithium hydroxide monohydrate (11 mg, 0.26 mmol). The mixture was then stirred for 1 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and then diluted with 1N aqueous hydrochloric acid until the pH was acidic and then extracted with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to afford 3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid (40 mg, 74%) as a tan solid: HR-ES-MS m/z calculated for C19H13NO4Cl2F2 [M+H]+ 428.0263, observed 428.0263.

Fuente