Acetonitrile → (4S,5R)-3-{[5-(5-Chloro-2-methoxypyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazolidin-2-one

HRID 531235Notes

Reaction equation

HRID 531235 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[C:9](#N)C.[Cl:12][C:13]1[CH:14]=[C:15]([C:21]2[C:22]([CH2:29][N:30]3[C@@H:34]([CH3:35])[C@@H:33]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]([F:46])([F:45])[F:44])[CH:37]=4)[O:32][C:31]3=[O:47])=[N:23][C:24](SC)=[N:25][CH:26]=2)[C:16]([O:19][CH3:20])=[N:17][CH:18]=1>O.COC(C)(C)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:21]2[C:22]([CH2:29][N:30]3[C@@H:34]([CH3:35])[C@@H:33]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]([F:44])([F:46])[F:45])[CH:37]=4)[O:32][C:31]3=[O:47])=[N:23][C:24]([S:1]([CH3:9])(=[O:6])=[O:2])=[N:25][CH:26]=2)[C:16]([O:19][CH3:20])=[N:17][CH:18]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10313463Potassium peroxymonosulphateHCID 118021393(4S,5R)-3-{[5-(5-Chloro-2-methoxypyridin-3-yl)-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazolidin-2-one2×

Product 1

HCID 90009163(4S,5R)-3-{[5-(5-Chloro-2-methoxypyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

Potassium peroxymonosulfate (972 mg, 1.581 mmol) was added to an acetonitrile (4 mL)/water (2 mL) solution of (4S,5R)-3-{[5-(5-chloro-2-methoxypyridin-3-yl)-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazolidin-2-one (INTERMEDIATE 19, 380 mg, 0.702 mmol) at 25° C. The reaction was stirred for 16 hours at 25° C. followed by dilution with 100 mL methyl-t-butyl ether and 100 mL water. The organic layer was washed with 100 mL of aqueous NaCl three times. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated to give the title compound as a white solid, which can be used without further purification. LCMS (M+H)+: 573.3.

Workup

  1. washThe organic layer was washed with 100 mL of aqueous NaCl three times
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f604e7edf3d74b60b123c7d36e2d762f
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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