Hydrogen Peroxide → HCID 22915511, compound

HRID 1377928Notes

Reaction equation

HRID 1377928 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH:9]([CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1)C(N1[C@@H](CC2C=CC=CC=2)COC1=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:42]O.[Li+].[OH-].C1[CH2:50][O:49]CC1>>[C:1]([O:5][C:6]([CH2:8][CH:9]([CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)=[CH:32][CH:33]=1)[C:50]([OH:49])=[O:42])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 22876690HCID 22876690, compound

Product 1

HCID 22915511HCID 22915511, compoundYield 52%

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution in THF (200 mL) of N-[2-tert-butyloxycarbonylmethyl-4-(4-(4-cyanophenyl)phenoxy)butanoyl]-(S)-(-)-4-benzyl-2-oxazolidinone (7.05 g, 12.7 mmol) was added 30% aqueous H2O2 (3.0 mL, 50.8 mmol) and 1M aqueous LiOH (20.3 mL, 20.3 mmol) and the reaction mixture was stirred for one hour. The reaction mixture was quenched with saturated aqueous NaHSO3 and diluted with dichloromethane. The aqueous phase was made basic with aqueous 2N NaOH and extracted twice with dichloromethane. The organic extracts were discarded and the aqueous phase was cooled to 0° C. and acidified with aqueous 2N HCl. The aqueous phase was extracted with dichloromethane and THF/dichloromethane. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (dichloromethane/10% THF/1% methanol) gave 2-tert-butyloxycarbonylmethyl-4-[4-(4-cyanophenyl)phenoxy]butanoic acid (2.6 g, 52%).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NaHSO3
  2. additiondiluted with dichloromethane
  3. extractionextracted twice with dichloromethane
  4. extractionThe aqueous phase was extracted with dichloromethane and THF/dichloromethane
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ae1e2cafa234b70a2d6f48eb77bfff1
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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