Water → (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-(5-isopropyl-2-methoxypyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 531232Notes

Reaction equation

HRID 531232 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[C:9](#N)C.O.[F:13][C:14]([F:53])([F:52])[C:15]1[CH:16]=[C:17]([C@H:25]2[O:29][C:28](=[O:30])[N:27]([CH2:31][C:32]3[C:37]([C:38]4[C:39]([O:47][CH3:48])=[N:40][CH:41]=[C:42]([CH:44]([CH3:46])[CH3:45])[CH:43]=4)=[CH:36][N:35]=[C:34](SC)[N:33]=3)[C@H:26]2[CH3:51])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1>C(OC)(C)(C)C>[F:23][C:21]([F:22])([F:24])[C:19]1[CH:18]=[C:17]([C@H:25]2[O:29][C:28](=[O:30])[N:27]([CH2:31][C:32]3[C:37]([C:38]4[C:39]([O:47][CH3:48])=[N:40][CH:41]=[C:42]([CH:44]([CH3:45])[CH3:46])[CH:43]=4)=[CH:36][N:35]=[C:34]([S:1]([CH3:9])(=[O:6])=[O:2])[N:33]=3)[C@H:26]2[CH3:51])[CH:16]=[C:15]([C:14]([F:13])([F:53])[F:52])[CH:20]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6342AcetonitrileHCID 10313463Potassium peroxymonosulphateHCID 118021417(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-(5-isopropyl-2-methoxypyridin-3-yl)-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 90009173(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-(5-isopropyl-2-methoxypyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

Potassium peroxymonosulfate (4.08 g, 6.63 mmol) was added to an acetonitrile (12 mL) and water (8 mL) suspension of title compound from step A above (1.66 g, 2.76 mmol). This was then stirred for 2 hours at 25° C., at which time LCMS showed complete conversion to product. The reaction was diluted with methyl t-butyl ether (50 mL) and poured into water (100 mL). The organic layer was washed twice with 100 mL aqueous NaCl, then dried over sodium sulfate, filtered and the filtrate concentrated to give a white solid, which can be used without further purification. LCMS (M+H)+: 633.4. 1H NMR (CDCl3, 500 MHz) δ 8.75 (s, 1H), 8.24 (d, J=2.2 Hz, 1H), 7.92 (s, 1H), 7.80 (s, 2H), 7.49 (d, J=2.2 Hz, 1H), 5.89 (d, J=8.3 Hz, 1H), 4.93 (d, J=17.7 Hz, 1H), 4.59 (m, 1H), 4.26 (d, J=17.7 Hz, 1H), 3.98 (s, 3H), 3.43 (s, 3H), 3.02 (m, 1H), 1.33 (d, J=6.9 Hz, 6H), 0.80 (d, J=6.6 Hz, 3H).

Workup

  1. washThe organic layer was washed twice with 100 mL aqueous NaCl
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customto give a white solid, which
  6. customcan be used without further purification

Sources & evidence

ORD record
ord-3b802c422e1b4b80acc80229659ea91b
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

Loading…