Reacción #60577

Ecuación de reacción

2-methoxy-17-oxo-estra-1,3,5(10)-trien-3-yl sulfamate

hydroxylamine hydrochloride

sodium bicarbonate

water

→

2-methoxy-(E)-17-(oximino)-estra-1,3,5(10)-trien-3-yl sulfamate

Rendimiento 74.9%

2-Methoxy-(E)-17-(oximino)-estra-1,3,5(10)-trien-3-yl Sulfamate

Rendimiento 74.9%

Disolventes

methanol

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for one hour
2. 2
   OtroAfter phase separation
3. 3
   Extracciónthe aqueous phase was extracted twice more with 15 ml each of ethyl acetate
4. 4
   LavadoThe combined organic phases were first washed with 15 ml of 0.5N HCl
5. 5
   Secadowith saturated NaCl solution, dried on sodium sulfate
6. 6
   Concentraciónconcentrated by evaporation in a rotary evaporator
7. 7
   OtroThe crude product was purified by flash chromatography (toluene/ethyl acetate 3:1)

Procedimiento

A suspension of 570 mg of 2-methoxy-17-oxo-estra-1,3,5(10)-trien-3-yl sulfamate, 365 mg of hydroxylamine hydrochloride and 441 mg of sodium bicarbonate in 8 ml of methanol was stirred under reflux for one hour. Then, it was mixed with 30 ml each of water and ethyl acetate. After phase separation, the aqueous phase was extracted twice more with 15 ml each of ethyl acetate. The combined organic phases were first washed with 15 ml of 0.5N HCl and then with saturated NaCl solution, dried on sodium sulfate and concentrated by evaporation in a rotary evaporator. The crude product was purified by flash chromatography (toluene/ethyl acetate 3:1). 444 mg (73%) of 2-methoxy-(E)-17-(oximino)-estra-1,3,5(10)-trien-3-yl sulfamate (17) was obtained as colorless crystals.

Fuente