m-Chloroperbenzoic acid → HCID 54274875, compound

HRID 1900184Notes

Reaction equation

HRID 1900184 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:20][CH:21]([NH:23][C:24](=[O:36])[C@H:25]([CH:33]([CH3:35])[CH3:34])[NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH3:22])=[CH:15][CH:14]=1>C(Cl)Cl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:20][CH:21]([NH:23][C:24](=[O:36])[C@H:25]([CH:33]([CH3:35])[CH3:34])[NH:26][C:27]([O:29][CH:30]([CH3:31])[CH3:32])=[O:28])[CH3:22])=[O:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53780799HCID 53780799, compound

Product 1

HCID 54274875HCID 54274875, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 g of m-chloroperbenzoic acid was added to a solution containing 2.5 g of N1 -[2-(4-fluorophenylthio)-1-methylethyl]-N2 -isopropoxycarbonyl-L-valinamide dissolved in 50 ml of methylene chloride, at 0° C. After the mixture was stirred for 5 hours at room temperature, the reaction mixture was filtered. The filtrate was washed successively with a saturated aqueous solution of potassium carbonate and water, the organic layer was dried over anhydrous sodium sulfate and the methylene chloride was removed under reduced pressure. The obtained residue was purified by column chromatography on silica gel, thus obtaining 1.8 g of the desired product in the form of a colorless prism-shaped crystal (yield: 69%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washThe filtrate was washed successively with a saturated aqueous solution of potassium carbonate and water
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe methylene chloride was removed under reduced pressure
  5. customThe obtained residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-94f328faf1bb4cb2a47113c58509d247
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

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