m-Chloroperbenzoic acid → 3-Cephem 1-oxide

HRID 1606514Notes

Reaction equation

HRID 1606514 reaction equation
[S:1]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[CH2:4][CH:3]=[CH:2]1.S1[C@@H]2CC(=[O:18])N2C=CC1.ClC1C=CC=C(C(OO)=O)C=1>>[S:1]1(=[O:18])[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[CH:4]=[CH:3][CH2:2]1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 208364673-CephemHCID 714080692-Cephem2×

Product 1

HCID 678652903-Cephem 1-oxide

Procedure

The rearrangement of 2-cephem derivatives to the corresponding 3-cephem compounds is accomplished by an oxidation-reduction procedure well documented in the cephalosporin art. Generally, this procedure is carried out by first oxidizing the 2-cephem compound with, e.g., m-chloroperbenzoic acid, to give the corresponding 3-cephem 1-oxide derivative which is subsequently reduced via a trivalent phosphorous compound, such as phosphorous tribromide or phosphorous trichloride, preferably using dimethylformamide as a solvent.

Sources & evidence

ORD record
ord-e169ccfe1cb34a1c9bad2af3d80af362
Source dataset
uspto-grants-1976_04
Patent number
US03953436

Reaction notes

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