Methanesulfonyl chloride → HCID 57114966, compound

HRID 654868Notes

Reaction equation

HRID 654868 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C@:14]([OH:26])([C@@H:21]([CH3:25])[C@@H:22]([OH:24])[CH3:23])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1>N1C=CC=CC=1>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C@:14]([OH:26])([C@@H:21]([CH3:25])[C@@H:22]([O:24][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:23])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57248251HCID 57248251, compound

Product 1

HCID 57114966HCID 57114966, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

140 mg (1.22 mmole) of methanesulfonyl chloride were added at 0° C. to a solution of 213 mg (0.72 mmole) of (2R*,3S*,4S*)-2-(2,4-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-2,4-pentanediol [prepared as described in step (b) above] in 4 ml of pyridine, and the mixture was stirred for 2.5 hours. At the end of this time, the pyridine was removed by distillation under reduced pressure. The resulting residue was mixed with a dilute aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and freed from the solvent by evaporation under reduced pressure, to afford 270 mg of the title compound as an oil.

Workup

  1. customAt the end of this time, the pyridine was removed by distillation under reduced pressure
  2. additionThe resulting residue was mixed with a dilute aqueous solution of sodium hydrogencarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customfreed from the solvent by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9e3f6f32d6b642be8f7bf6d3efd2d053
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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