Hydrogen Peroxide → HCID 86680344, compound

HRID 83485Notes

Reaction equation

HRID 83485 reaction equation
O.[OH-].[Li+].OO.C([C@@H]1COC(=O)N1[C:19]([C@H:21]1[C@H:25]([CH3:26])[C:24](=[O:27])[N:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[O:37][CH3:38])[CH2:22]1)=[O:20])C1C=CC=CC=1.S([O-])(O)=[O:40].[Na+]>O.O1CCCC1>[CH3:38][O:37][C:30]1[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:29]=1[CH2:28][N:23]1[C:24](=[O:27])[C@@H:25]([CH3:26])[C@H:21]([C:19]([OH:20])=[O:40])[CH2:22]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 23665763Sodium BisulfiteHCID 86680347(R)-4-benzyl-3-[(trans)-1-(2,4-dimethoxybenzyl)-4-methyl-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinone

Product 1

HCID 86680344HCID 86680344, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium hydroxide monohydrate (1.26 g) in water (30 ml) was added dropwise 30 wt % aqueous solution of hydrogen peroxide (7.0 ml) under ice-cooling, and the mixture was stirred for 10 minutes. To this reaction solution was added tetrahydrofuran 30 ml, and then a solution of the low-polarity component of (R)-4-benzyl-3-[(trans)-1-(2,4-dimethoxybenzyl)-4-methyl-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinone (11.4 g) in tetrahydrofuran (90 ml) was added dropwise thereto, and then the mixture was stirred for additional 1 hour. To this reaction solution was added dropwise a solution of sodium hydrogen sulfite (7.18 g) in water (50 ml), and then the mixture was warmed to room temperature, and stirred for 1 hour. This mixture was extracted with ethyl acetate, and the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=1/1 to 1/2, chloroform/methanol=5/1) to give a crude product of the titled compound (8.11 g). An analysis of the solid by HPLC analysis condition 1 showed that an isomer with shorter retention time was a main product.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for additional 1 hour
  3. stirringstirred for 1 hour
  4. extractionThis mixture was extracted with ethyl acetate
  5. washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=1/1 to 1/2, chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-80c803f6f0904d3da084c9ff3951ad76
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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