m-Chloroperbenzoic acid → HCID 15611132, compound

HRID 1253159Notes

Reaction equation

HRID 1253159 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([S:14][C:15]1[S:16][C@@H:17]2[C@H:34]([C:35]([OH:38])([CH3:37])[CH3:36])[C:33](=[O:39])[N:18]2[C:19]=1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:21])[CH3:13]>C(Cl)Cl>[CH2:12]([S:14]([C:15]1[S:16][C@@H:17]2[C@H:34]([C:35]([OH:38])([CH3:36])[CH3:37])[C:33](=[O:39])[N:18]2[C:19]=1[C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=1)=[O:21])=[O:6])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15611130HCID 15611130, compound

Product 1

HCID 15611132HCID 15611132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 85% m-chloroperoxybenzoic acid (112 mg, 0.55 mmol) in CH2Cl2 (2.5 ml) is added dropwise over 5 mins. to an ice-cold, stirring solution of p-nitrobenzyl (5R,6R)-2-ethylthio-6-(2-hydroxy-2-propyl)-pen-2-em-3-carboxylate (212 mg, 0.5 mmol) in CH2Cl2 (5 ml). The mixture is stirred for 1 hour at 0°, then treated with excess Amberlyst-21 resin and stirred 5 minutes longer. The mixture is filtered and the filtrate is evaporated under vacuum to provide the crude product.

Workup

  1. additiontreated with excess Amberlyst-21 resin
  2. stirringstirred 5 minutes longer
  3. filtrationThe mixture is filtered
  4. customthe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-b416a0f8008f4e7888a95a1006edfbac
Source dataset
uspto-grants-1988_05
Patent number
US04748162

Reaction notes

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