m-Chloroperbenzoic acid → HCID 70504397, compound

HRID 1463142Notes

Reaction equation

HRID 1463142 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]([NH:20][CH:21]1[C:50](=[O:51])[N:23]2[CH:24]([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[C:25]([CH2:29][O:30][C:31](=[O:33])[CH3:32])=[C:26]([CH3:28])[S:27][C@H:22]12)=[O:19]>C(Cl)Cl>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]([NH:20][CH:21]1[C:50](=[O:51])[N:23]2[C:24]([C:34]([O:36][CH:37]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:35])=[C:25]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[CH:26]([CH3:28])[S:27](=[O:9])[C@H:22]12)=[O:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70504358HCID 70504358, compound

Product 1

HCID 70504397HCID 70504397, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 13.7 g of m-chloroperbenzoic acid in 50 ml of CH2Cl2 was added to a solution of 37.3 g of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-acetoxymethylceph-2-em-4-carboxylate in 300 ml of CH2Cl2 at -20° C., and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was washed with 5% aqueous NaHCO3 and saturated aqueous NaCl solutions, and dried over MgSO4, followed by distilling off the solvent under reduced pressure. AcOEt.Et2O (1:3) was added to the residue, thus yielding 32 g (84%) of crystals of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-acetoxymethylceph-3-em-4-carboxylate 1-oxide.

Workup

  1. washThe reaction solution was washed with 5% aqueous NaHCO3 and saturated aqueous NaCl solutions
  2. dry with materialdried over MgSO4
  3. distillationby distilling off the solvent under reduced pressure
  4. additionEt2O (1:3) was added to the residue

Sources & evidence

ORD record
ord-736a4331eb444c5492dcca84f068b398
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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