Methanesulfonyl chloride → HCID 21356564, compound

HRID 1167493Notes

Reaction equation

HRID 1167493 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][OH:20])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[C:12]([CH3:13])=[CH:11][N:10]=[CH:9]1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][O:20][S:23]([CH3:22])(=[O:25])=[O:24])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[C:12]([CH3:13])=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 21356563HCID 21356563, compound

Product 1

HCID 21356564HCID 21356564, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(3-Fluoro-4-(5-methyl-imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (0.86 g, 2.96 mmol) was stirred in a mixture of pyridine (30 ml) and triethylaminc (0.36 g, 3.55 mmol) under nitrogen in an ice-bath. Methanesulfonyl chloride (0.37 g, 3.26 mmol) was added dropwise, and the mixture stirrd for 18 hours, allowing the temperature to rise to ambient. Solvent was evaporated. and the residue dissolved in dichloromethane (50 ml), and washed with aqueous sodium bicarbonate (5%, 25 ml), water (2×25 ml), brine (20 ml), and dried (magnesium sulfate). The residue after evaporation was triturated with diethyl ether to give the title product (0.68 g).

Workup

  1. customSolvent was evaporated
  2. dissolutionand the residue dissolved in dichloromethane (50 ml)
  3. washwashed with aqueous sodium bicarbonate (5%, 25 ml), water (2×25 ml), brine (20 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customThe residue after evaporation
  6. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-ddd0a0278db943a283cf1b374531e659
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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