Acetonitrile → HCID 20718632, compound

Participants

Reaction Steps

52 mg (0.19 mM) of 13β-methyl-1,3,5(10)-gonatrien-3,17α-diol are dissolved 10 ml acetonitrile accompanied by heat and 500 mg of (anhydrous) Na2CO3 are added. After the solution is cooled, 30 mg (0.26 mM) of H2NSO2Cl are added and the solution is stirred vigorously. At one-hour intervals, 9 portions of H2NSO2Cl are added for every 10 mg. After 9 hours, the solution is worked up by stirring in diluted hydrochloric acid solution and the steroid is extracted with ether. The residue remaining after the concentration of the extract is absorbed in 4 ml of an acetonitrile/ethanol mixture (3:1) and separated by preparative HPLC (ET 125/8/4 Nucleosil 120-5C18 Macherey-Nagel, RT7.0) using acetonitrile as eluent. After concentration of the fraction with the Rt=7.0 (Rt=0.2; gel benzene; acetone=4:1) or Rt=8.1 (Rf=0.22 gel, benzene/acetone 4:1), 28.9 mg of the 3,17α-disulfamate (35.4%) and 9.8 mg (14.6%) of the 3 monosulfamate are isolated in the form of white powder.

Provenance & Evidence