m-Chloroperbenzoic acid → HCID 57039536, compound

HRID 1253161Notes

Reaction equation

HRID 1253161 reaction equation
[CH2:1]([S:3][C:4]1[S:5][C@@H:6]2[C@@H:23]([O:24][CH3:25])[C:22](=[O:26])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:32]>CN(C=O)C.C(Cl)Cl>[CH2:1]([S:3]([C:4]1[S:5][C@@H:6]2[C@@H:23]([O:24][CH3:25])[C:22](=[O:26])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)=[O:10])=[O:32])[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57055708HCID 57055708, compound

Product 1

HCID 57039536HCID 57039536, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of p-nitrobenzyl (5R,6S)-2-ethylthio-6-methoxy-pen-2-em-3-carboxylate (96 mg, 0.24 mmol) in anhydrous DMF (1.2 ml) is diluted with CH2Cl2 (2.4 ml) and cooled in an ice-bath. A solution of 85% m-chloroperoxybenzoic acid (51 mg, 0.25 mmol) in CH2Cl2 (1.2 ml) is added dropwise over 2 minutes to the cold, stirring solution. The resulting mixture is kept at 0° for 60 minutes, and then treated with excess Amberlyst-21 resin and stirred and additional 5 minutes. The mixture is filtered and the filtrate is diluted with CH2Cl2 and washed with 5 portions of H2O. The organic phase is dried over MgSO4, filtered, and evaporated under vacuum to give a crude residue of the title compound which is purified by rapid chromatography on silica gel.

Workup

  1. temperaturecooled in an ice-bath
  2. additiontreated with excess Amberlyst-21 resin
  3. stirringstirred and additional 5 minutes
  4. filtrationThe mixture is filtered
  5. additionthe filtrate is diluted with CH2Cl2
  6. washwashed with 5 portions of H2O
  7. dry with materialThe organic phase is dried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-19ff44868ed245ada17c555db14e5c0f
Source dataset
uspto-grants-1988_05
Patent number
US04748162

Reaction notes

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