m-Chloroperbenzoic acid → HCID 57088416, compound

HRID 1253157Notes

Reaction equation

HRID 1253157 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13][C:14]1[S:15][C@@H:16]2[C@@H:33]([CH2:34][CH3:35])[C:32](=[O:36])[N:17]2[C:18]=1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl.C1COCC1.CCOC(C)=O>[CH3:12][S:13]([C:14]1[S:15][C@@H:16]2[C@@H:33]([CH2:34][CH3:35])[C:32](=[O:36])[N:17]2[C:18]=1[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=1)=[O:20])=[O:6]

Participants

6

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57020813HCID 57020813, compound

Product 1

HCID 57088416HCID 57088416, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 85% m-chloroperoxy benzoic acid (53 mg, 0.26 mmol) in CH2Cl2 (1 ml) is added dropwise over a few minutes to an ice-cold, stirring solution of p-nitrobenzyl (5R,6S)-2-methylthio-6-ethyl-pen-2-em-3-carboxylate (94 mg, 0.25 mmol) in anhydrous THF (2 ml). The resulting solution is stirred an additional 30 minutes at 0°, then diluted with EtOAc and washed with H2O, 5% aqueous NaHCO3, H2O, and brine. The organic phase is dried with MgSO4, filtered, and evaporated in vacuo to provide the title compound as a mixture of sulfoxide isomers.

Workup

  1. washwashed with H2O, 5% aqueous NaHCO3, H2O, and brine
  2. dry with materialThe organic phase is dried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ab4cda98b778447ba49c6522c14b3755
Source dataset
uspto-grants-1988_05
Patent number
US04748162

Reaction notes

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