Water → HCID 90009175, compound

HRID 531259Notes

Reaction equation

HRID 531259 reaction equation
[F:1][C:2]([F:50])([F:49])[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]([C:26]4[CH:27]=[C:28]([C:34]5[C:43]([CH3:44])=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][C:35]=5[CH3:45])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22](SC)[N:21]=3)[C@H:14]2[CH3:48])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.[S:52]([O-:57])(O[O-])(=O)=[O:53].[K+].[K+].[C:60](#N)C>>[F:11][C:9]([F:10])([F:12])[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]([C:26]4[CH:27]=[C:28]([C:34]5[C:35]([CH3:45])=[CH:36][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:42][C:43]=5[CH3:44])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22]([S:52]([CH3:60])(=[O:57])=[O:53])[N:21]=3)[C@H:14]2[CH3:48])[CH:4]=[C:3]([C:2]([F:1])([F:50])[F:49])[CH:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 10313463Potassium peroxymonosulphateHCID 118021675Methyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfanyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzoate2×

Product 1

HCID 90009175HCID 90009175, compound

Procedure

Methyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylthio)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzoate (INTERMEDIATE 43, 1.05 g, 1.457 mmol) was dissolved in acetonitrile (10.2 mL). Water (4.4 mL) was added, followed by potassium peroxymonosulfate (2.24 g, 3.64 mmol). The reaction was allowed to stir 16 hours, after which it was partitioned between ethyl acetate and brine. The organic was washed a second time with brine, dried over sodium sulfate, filtered and evaporated to give the title compound, which can be used without further purification. 1H NMR (CDCl3, 500 MHz): δ 8.75 (s, 1H), 8.16 (d, 1H), 7.89 (s, 1H), 7.83 (s, 2H), 7.77 (s, 2H), 7.42 (d, 1H), 5.88 (d, 1H), 4.92 (d, 1H), 4.62 (br, 1H), 4.25 (d, 1H), 4.04 (s, 3H), 3.94 (s, 3H), 3.41 (s, 3H), 2.17 (d, 6H), 0.81 (d, 3H).

Workup

  1. customafter which it was partitioned between ethyl acetate and brine
  2. washThe organic was washed a second time with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9f8993392bc64a5da3dbfa87527e0e54
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

Loading…