m-Chloroperbenzoic acid → HCID 67831553, compound

HRID 1885268Notes

Reaction equation

HRID 1885268 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C@H:15]3[S:14](=[O:42])[CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Product 1

HCID 67831553HCID 67831553, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To an ice cold solution of 7β-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (3.0 g; 6.16 mMol.) in dichloro-methane (50 ml) is added m-chloroperbenzoic acid (1.32 g: 1 Eq.), and the mixture is stirred for 1 hour under ice cooling. The reaction mixture is diluted with aqueous 5% sodium thiosulfate and extracted with dichloromethane. The extract is washed with aqueous sodium hydrogen carbonate, dried, and concentrated in vacuum to give 7β-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester 1-oxide (1.66 g). Yield: 53.5%.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with aqueous sodium hydrogen carbonate
  3. customdried
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-2f9042fdc5ec462e9c778bbb568aa247
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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