Reacción #95487

Ecuación de reacción

21-[3-(4-acetyloxyphenyl)-4-carboxy-1-oxobutoxy]-11β,18-epoxy-18-hydroxypregn-4-ene-3,20-dione

triethylamine

→

title compound

Rendimiento 68.6%

21-[4-Carboxy-3-(4-hydroxyphenyl)-1-oxobutoxy]-11β,18-epoxy-18-hydroxypregn-4-ene-3,20-dione

Rendimiento 68.6%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe methanol is then evaporated in vacuo
2. 2
   workup.ADDITIONthe residue is diluted with water (5.0 ml)
3. 3
   Extracciónextracted with ethyl acetate (three 5.0 ml portions)
4. 4
   LavadoThe ethyl acetate solution is washed with brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Otroevaporated

Procedimiento

A solution of 21-[3-(4-acetyloxyphenyl)-4-carboxy-1-oxobutoxy]-11β,18-epoxy-18-hydroxypregn-4-ene-3,20-dione (130 mg) in anhydrous methanol (15 ml) containing triethylamine (0.2 ml) is allowed to stand at room temperature for 24 hours. The methanol is then evaporated in vacuo, the residue is diluted with water (5.0 ml), acidified with 10% hydrochloric acid and extracted with ethyl acetate (three 5.0 ml portions). The ethyl acetate solution is washed with brine, dried over anhydrous magnesium sulfate, evaporated and the residue is subjected to preparative thin-layer chromatography on silica gel plates (using chloroform-methanol, 9:1 for development) to isolate 83 mg of the title compound, melting point 145°-152° C., with consistent spectral data.

Fuente