반응 #60577

반응 방정식

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

수율 74.9%

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

수율 74.9%

용매

methanol

ethyl acetate

반응 조건

후처리

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

실험 절차

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.

출처