P-Toluenesulfonylhydrazide → 11beta-Methoxy-17-tosylhydrazono-estra-1,3,5(10)-trien-3-ol

HRID 2215943Notes

Reaction equation

HRID 2215943 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][C@@H:15]3[O:20][CH3:21])([CH3:13])[C:11](=O)[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[C:23]1([CH3:34])[CH:28]=[CH:27][C:26]([S:29]([NH:32][NH2:33])(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(O)C.C(O)(=O)C.O.CCCCCC>[CH3:21][O:20][C@H:15]1[CH2:14][C@@:12]2([CH3:13])[C@@H:8]([CH2:9][CH2:10][C:11]2=[N:33][NH:32][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:34])=[CH:24][CH:25]=2)(=[O:30])=[O:31])[C@H:7]2[C@H:16]1[C:17]1[CH:18]=[CH:19][C:2]([OH:1])=[CH:3][C:4]=1[CH2:5][CH2:6]2

Participants

7

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 1120881311beta-Methoxy-3-hydroxy-estra-1,3,5(10)-trien-17-one

Product 1

HCID 6952946511beta-Methoxy-17-tosylhydrazono-estra-1,3,5(10)-trien-3-ol

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

In a mixture of 6 ml of ethanol and 4 ml of glacial acetic acid, 1 g (3.3 mmol) of 3-hydroxy-11β-methoxy-estra-1,3,5(10)-trien-17-one and 0.7 g (3.8 mmol) of toluene-4-sulfonic acid hydrazide are refluxed. After a reaction time of about 5 hours at boiling heat, the reaction mixture is cooled, and the product is isolated in about 100 ml of water by addition in drops. By boiling the crude product in n-hexane, the water that is contained is azeotropically removed.

Workup

  1. temperatureare refluxed
  2. temperatureAfter a reaction time of about 5 hours at boiling heat
  3. temperaturethe reaction mixture is cooled
  4. customthe water that is contained is azeotropically removed

Sources & evidence

ORD record
ord-553214bdfaff459c866558982e8d0862
Source dataset
uspto-grants-2006_09
Patent number
US07109360B1

Reaction notes

Loading…