tert-Butyl methyl ether → 4-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfonyl)pyrimidin-5-yl]-4-methyl-1,3-thiazol-2-yl}-3-methylbenzoic acid

HRID 531266Notes

Reaction equation

HRID 531266 reaction equation
[F:1][C:2]([F:46])([F:45])[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[S:30][C:29]([C:31]5[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][C:32]=5[CH3:40])=[N:28][C:27]=4[CH3:41])=[CH:24][N:23]=[C:22](SC)[N:21]=3)[C@H:14]2[CH3:44])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[S:47]([O-:52])(O[O-])(=O)=[O:48].[K+].[K+].[CH3:55]OC(C)(C)C>C1COCC1.O>[F:46][C:2]([F:1])([F:45])[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[S:30][C:29]([C:31]5[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][C:32]=5[CH3:40])=[N:28][C:27]=4[CH3:41])=[CH:24][N:23]=[C:22]([S:47]([CH3:55])(=[O:52])=[O:48])[N:21]=3)[C@H:14]2[CH3:44])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 10313463Potassium peroxymonosulphateHCID 1180214914-{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]-4-methyl-1,3-thiazol-2-yl}-3-methylbenzoic acid2×

Product 1

HCID 900092914-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfonyl)pyrimidin-5-yl]-4-methyl-1,3-thiazol-2-yl}-3-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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]-4-methyl-1,3-thiazol-2-yl}-3-methylbenzoic acid (INTERMEDIATE 53, 2.2 g, 3.22 mmol), was dissolved in 10 mL of THF and 10 mL of water. Potassium peroxymonosulfate (5.11 g, 8.31 mmol) was added, and it was stirred at 60° C. for 2 hours. Then, it was worked up with water (100 mL) and t-butyl methyl ether (200 mL). The organic layer was concentrated and purified on a silica gel column, eluting with 60% ethyl acetate in hexanes to give the title compound as a slightly yellow solid. LCMS (M+1): 715.0 1H NMR (CDCl3, 500 MHz): δ 8.93 (s, 1H), 8.93 (s, 1H), 8.10 (s, 1H), 8.03 (d, 8.5 Hz, 1H), 7.93 (m, 2H), 7.82 (s, 2H), 6.00 (d, 8.5 Hz, 1H), 5.08 (d, 16.5 Hz, 1H), 4.67 (m, 1H), 4.31 (d, 16.6 Hz, 1H), 3.46 (s, 3H), 2.75 (s, 3H), 2.50 (s, 3H), 0.86 (d, 6.5 Hz, 3H).

Workup

  1. concentrationThe organic layer was concentrated
  2. custompurified on a silica gel column
  3. washeluting with 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-898b0a5f9e404a679fdad8d14152c146
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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