m-Chloroperbenzoic acid → HCID 88600876, compound

HRID 2413815Notes

Reaction equation

HRID 2413815 reaction equation
[CH:1]([NH:3][CH:4]1[C:31](=[O:32])[N:6]2[CH:7]([C:15]([O:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[C:8]([CH:11]=[C:12]([Br:14])[Br:13])=[CH:9][S:10][C@H:5]12)=[O:2].ClC1C=CC=C(C(OO)=[O:41])C=1>C(OCC)(=O)C>[CH:1]([NH:3][CH:4]1[C:31](=[O:32])[N:6]2[C:7]([C:15]([O:17][CH:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:16])=[C:8]([CH:11]=[C:12]([Br:13])[Br:14])[CH2:9][S:10](=[O:41])[C@H:5]12)=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 88600901HCID 88600901, compound

Product 1

HCID 88600876HCID 88600876, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of benzhydryl 7-formamido-3-(2,2-dibromovinyl)-2-cephem-4-carboxylate (4.2 g) in ethyl acetate (42 ml) was added a solution of m-chloroperbenzoic acid (1.72 g) in ethyl acetate at -20° to -10° C. and the resultant mixture was stirred at -10° C. for 45 minutes. The precipitates were collected by filtration to give benzhydryl 7-formamido-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate-1-oxide (1.9 g).

Workup

  1. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-87a2477ae3fc41dc8ba68077435e526e
Source dataset
uspto-grants-1988_01
Patent number
US04719206

Reaction notes

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