Hydrogen Peroxide → HCID 57754958, compound

HRID 226552Notes

Reaction equation

HRID 226552 reaction equation
C(C1COC(=O)N1[C:14](=[O:51])[CH:15]([C:20]1[CH:21]=[C:22]([C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=2)[CH:23]=[C:24]([NH:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=2[C:37]([F:40])([F:39])[F:38])[CH:25]=1)[CH2:16][CH:17]([CH3:19])[CH3:18])C1C=CC=CC=1.O[Li].[OH2:54].OO.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1.O>[F:38][C:37]([F:39])([F:40])[C:28]1[CH:29]=[CH:30][C:31]([C:33]([F:36])([F:34])[F:35])=[CH:32][C:27]=1[NH:26][C:24]1[CH:25]=[C:20]([C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:14]([OH:51])=[O:54])[CH:21]=[C:22]([C:41]2[CH:42]=[CH:43][C:44]([C:47]([F:48])([F:49])[F:50])=[CH:45][CH:46]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 86617044HCID 86617044, compound

Product 1

HCID 57754958HCID 57754958, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-benzyl-3-{2-[5-(2,5-bis-trifluoromethyl-phenylamino)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoyl}-oxazolidin-2-one (2.55 g, 3.53 mmol) in THF (15 mL) was added water (5 mL). The system was cooled to 0° C. To this cold solution was added LiOH.H2O (148 mg, 3.53 mmol) and 30% H2O2 (1.20 mL, 10.59 mmol,) and stirred at 0° C. for 15 min. The excess H2O2 was quenched by adding 1.5 M aqueous Na2SO3 solution (7.06 mL, 10.59 mmol) and stirred at room temperature for 10 min. The organic solvent was removed in vacuo. The resulting liquid was acidified to pH=2 by adding 1 N aqueous HCl solution. The aqueous layer was extracted with EtOAc (3×50 mL) and dried (MgSO4). The mixture was concentrated in vacuo to receive a crude mixture which was purified by ISCO silica gel column chromatography to yield (R) 2-[5-(2,5-Bis-trifluoromethyl-phenylamino)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid (1.15 g, 58%).

Workup

  1. customThe excess H2O2 was quenched
  2. stirringstirred at room temperature for 10 min
  3. customThe organic solvent was removed in vacuo
  4. additionby adding 1 N aqueous HCl solution
  5. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationThe mixture was concentrated in vacuo
  8. customwas purified by ISCO silica gel column chromatography

Sources & evidence

ORD record
ord-d654aa87389c43f18d5118111d68e8ad
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

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