tert-Butyl methyl ether → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 531228Notes

Reaction equation

HRID 531228 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([Br:26])=[CH:24][N:23]=[C:22](SC)[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[S:32]([O-:37])(O[O-])(=O)=[O:33].[K+].[K+].[CH3:40]OC(C)(C)C>C(#N)C.O>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([Br:26])=[CH:24][N:23]=[C:22]([S:32]([CH3:40])(=[O:37])=[O:33])[N:21]=3)[C@H:14]2[CH3:29])[CH:4]=[C:3]([C:2]([F:1])([F:31])[F:30])[CH:8]=1

Participants

6

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 10313463Potassium peroxymonosulphateHCID 57576287(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one2×

Product 1

HCID 86704625(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-oneYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfanyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 8, 10 g, 18.86 mmol) in acetonitrile (25 mL) and water (25 mL) was added potassium peroxymonosulfate (27.8 g, 45.3 mmol). After it was stirred at room for 14 hours, LCMS showed complete conversion of the starting material. It was distributed between water (200 mL) and t-butyl methyl ether (300 mL). The organic layer was washed with water (200 mL) and brine, dried over sodium sulfate, filtered and the filtrate concentrated to get the title compound (10.2 g, 96% yield) as a brightly white solid. LCMS (M+H)+: 564.05. 1H NMR (CDCl3, 500 MHz): δ 8.99 (s, 1H), 7.93 (s, 1H), 7.84 (s, 2H), 6.02 (d, 8.5 Hz, 1H), 5.14 (d, 18.5 Hz, 1H), 4.56 (m, 1H), 4.42 (d, 18.0 Hz, 1H), 3.37 (S, 3H), 0.86 (d, 6.5 Hz, 3H).

Workup

  1. washThe organic layer was washed with water (200 mL) and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-bbaaa807f5c24d0e9cdc9ab5afcdcf02
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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