Hydrogen Peroxide → HCID 58003529, compound

HRID 426363Notes

Reaction equation

HRID 426363 reaction equation
C(C1COC(=O)N1[C:14](=[O:46])[CH:15]([C:20]1[CH:21]=[C:22]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[CH:25]=1)[CH2:16][CH:17]([CH3:19])[CH3:18])C1C=CC=CC=1.O[Li].[OH2:49].OO.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1.O>[F:33][C:32]([F:34])([F:35])[C:29]1[CH:30]=[CH:31][C:26]([C:24]2[CH:25]=[C:20]([C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:14]([OH:46])=[O:49])[CH:21]=[C:22]([C:36]3[CH:37]=[CH:38][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:40][CH:41]=3)[CH:23]=2)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 86616209HCID 86616209, compound

Product 1

HCID 58003529HCID 58003529, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-benzyl-3-[2-(4,4″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-4-methyl-pentanoyl]-oxazolidin-2-one (3.66 g, 5.7 mmol) in THF (24 mL) was added water (8 mL). The system was cooled to 0° C. To this cold solution was added LiOH.H2O (240 mg, 5.7 mmol) and 30% H2O2 (1.95 mL, 17.2 mmol), and stirred at 0° C. for 15 min. The excess H2O2 was quenched by adding 1.5 M aqueous Na2SO3 solution (11.5 mL, 17.2 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-(4,4″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-4-methyl-pentanoic acid (2.5 g, 92%).

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-1324d4a84db546219777e44cd9501732
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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