m-Chloroperbenzoic acid → Benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate-1-oxide

HRID 64747Notes

Reaction equation

HRID 64747 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([CH2:18][C:19]([NH:21][CH:22]2[C:49](=[O:50])[N:24]3[CH:25]([C:33]([O:35][CH:36]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])[C:26]([CH:29]=[C:30]([Cl:32])[Cl:31])=[CH:27][S:28][C@H:23]23)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)(=O)C>[C:12]1([CH2:18][C:19]([NH:21][CH:22]2[C:49](=[O:50])[N:24]3[C:25]([C:33]([O:35][CH:36]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[O:34])=[C:26]([CH:29]=[C:30]([Cl:31])[Cl:32])[CH2:27][S:28](=[O:9])[C@H:23]23)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 88625624HCID 88625624, compound

Product 1

HCID 88625126Benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate-1-oxideYield 42.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (7 g) in ethyl acetate (35 ml) was added to a solution of benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-2-cephem-4-carboxylate (15 g) in ethyl acetate (75 ml) under ice-cooling and the mixture was stirred at the same temperature for an hour. The precipitates were collected by filtration to give benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate-1-oxide (6.57 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-3d28ec22631c49fbb7e9d1fa971a4369
Source dataset
uspto-grants-1986_09
Patent number
US04609730

Reaction notes

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