Methanesulfonyl chloride → HCID 15513553, compound

HRID 968185Notes

Reaction equation

HRID 968185 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:21])=[CH:8][C:9]=1[CH2:10][CH2:11]2.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([O:21][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:8][C:9]=1[CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15513552HCID 15513552, compound

Product 1

HCID 15513553HCID 15513553, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

28.84 g of 11β-fluoro-1,3,5(10)-estratrien-3-ol-17-one (100 mmol) is dissolved in 200 ml of pyridine, cooled in an ice bath, 20 ml of methanesulfonic acid chloride is added in drops, and it is stirred for 2 hours at room temperature. Then, it is stirred into 2.5 liters of ice water, and after two hours of stirring, it is filtered off. The solid residue is dissolved in dichloromethane, the solution is shaken out with 1N hydrochloric acid, water and saturated common salt solution and dried with Na2SO4. After the solvent is drawn off, the residue is 37 g, and after crystallization from methanol, 33.6 g of 11β-fluoro-3-mesyloxy-estra-1,3,5(10)-trien-17-one (91% of theory), flash point, is obtained.

Workup

  1. temperaturecooled in an ice bath
  2. stirringafter two hours of stirring
  3. filtrationit is filtered off
  4. dissolutionThe solid residue is dissolved in dichloromethane
  5. stirringthe solution is shaken out with 1N hydrochloric acid, water and saturated common salt solution
  6. dry with materialdried with Na2SO4
  7. customafter crystallization from methanol, 33.6 g of 11β-fluoro-3-mesyloxy-estra-1,3,5(10)-trien-17-one (91% of theory), flash point
  8. customis obtained

Sources & evidence

ORD record
ord-92c64ff718f54ac69bff2d77bebf903a
Source dataset
uspto-grants-2005_10
Patent number
US06958327B1

Reaction notes

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