Acetonitrile → HCID 20718632, compound

HRID 1250461Notes

Reaction equation

HRID 1250461 reaction equation
[CH3:1][C@:2]12[CH2:10][CH2:9][C@@H:8]3[C:11]4[CH:12]=[CH:13][C:14]([OH:19])=[CH:15][C:16]=4[CH2:17][CH2:18][C@H:7]3[C@@H:6]1[CH2:5][CH2:4][C@H:3]2[OH:20].C(#N)C.C([O-])([O-])=O.[Na+].[Na+].[NH2:30][S:31](Cl)(=[O:33])=[O:32]>Cl>[S:31]([O:19][C:14]1[CH:13]=[CH:12][C:11]2[C@H:8]3[CH2:9][CH2:10][C@@:2]4([CH3:1])[C@H:6]([C@@H:7]3[CH2:18][CH2:17][C:16]=2[CH:15]=1)[CH2:5][CH2:4][C@H:3]4[O:20][S:31](=[O:33])(=[O:32])[NH2:30])(=[O:33])(=[O:32])[NH2:30]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 24499Chlorosulfamic acid2×HCID 6857017alpha-Estradiol

Product 1

HCID 20718632HCID 20718632, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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.

Workup

  1. temperatureby heat
  2. temperatureAfter the solution is cooled
  3. extractionthe steroid is extracted with ether
  4. customis absorbed in 4 ml of an acetonitrile/ethanol mixture (3:1)
  5. customseparated by preparative HPLC (ET 125/8/4 Nucleosil 120-5C18 Macherey-Nagel, RT7.0)

Sources & evidence

ORD record
ord-6d96e2ffea8947268fcee3d6f9b3961a
Source dataset
uspto-grants-2002_01
Patent number
US06339079B1

Reaction notes

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