反応 #60577

反応方程式

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

収率 74.9%

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

収率 74.9%

溶媒

methanol

ethyl acetate

反応条件

後処理

1. 1
   温度under reflux for one hour
2. 2
   その他After phase separation
3. 3
   抽出the aqueous phase was extracted twice more with 15 ml each of ethyl acetate
4. 4
   洗浄The combined organic phases were first washed with 15 ml of 0.5N HCl
5. 5
   乾燥with saturated NaCl solution, dried on sodium sulfate
6. 6
   濃縮concentrated by evaporation in a rotary evaporator
7. 7
   その他The crude product was purified by flash chromatography (toluene/ethyl acetate 3:1)

実験手順

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.

出典