Reacción #65120

Ecuación de reacción

sodium hydroxide

erythromycin A

sodium acetate

ammonium hydroxide

iodine

→

N-demethylerythromycin A

Disolventes

methanol water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONby pouring it
2. 2
   ExtracciónThe reaction mixture was extracted with ethyl acetate
3. 3
   Extracciónthe organic extract
4. 4
   Lavadowas washed with ammonium hydroxide-
5. 5
   workup.ADDITIONcontaining water
6. 6
   Concentraciónconcentrated
7. 7
   Otroafter removal of the solvent
8. 8
   Otrowas recrystallized from acetone/ammonium hydroxide solution 50:3

Procedimiento

20 g of erythromycin A (=27.2 mmole) and 11.2 g (=136.2 mmole) of sodium acetate were dissolved in 200 ml of an 8:2 methanol/water mixture. The solution was heated to 47° C. Then 6.9 g (=136.2 mmole) of iodine were added. The pH was kept at 8 to 9 by adding dilute aqueous sodium hydroxide solution. After 3 hours, the reaction mixture was worked up by pouring it into a mixture of 1 liter of water and 20 ml of ammonium hydroxide solution. The reaction mixture was extracted with ethyl acetate, and the organic extract was washed with ammonium hydroxide-containing water and concentrated. The crude product remaining after removal of the solvent was recrystallized from acetone/ammonium hydroxide solution 50:3. Melting point 143°-148° C.

Fuente