Potassium Bromide → Benzhydryl 7-(2-thienylacetamido)-7-methoxy-3-acetoxymethyl-3-cephem-4-carboxylate

HRID 1657708Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:36][CH3:37])[C:34](=[O:35])[N:12]2[C:13]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:14]([CH3:17])[CH2:15][S:16][C@H:11]12)=[O:8].[Br-].[K+]>C(O)(=O)C.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:36][CH3:37])[C:34](=[O:35])[N:12]2[C:13]([C:18]([O:20][CH:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:19])=[C:14]([CH2:17][O:20][C:18](=[O:19])[CH3:13])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

Conditions

Temperature: 70 °C

Procedure

Manganese (III) acetate (5.0 g.) in acetic acid (60 ml.) is heated to 70°C. under nitrogen. To the stirred solution is added benzhydryl 7-(2-thienylacetamido)-7-methoxy-3-methyl-3-cephem-4-carboxylate (4.0 g.) and potassium bromide (0.5 g.). The solution is maintained at 70°C. for about eight hours. The reaction mixture is cooled and manganese (II) acetate is filtered from the cooled solution. The solvent is removed under vacuum to afford benzhydryl 7-(2-thienylacetamido)-7 -methoxy-3-acetoxymethyl-3-cephem-4-carboxylate.

Workup

temperatureThe reaction mixture is cooled
filtrationmanganese (II) acetate is filtered from the cooled solution
customThe solvent is removed under vacuum

Sources & evidence

ORD record: ord-24ca7da60ba6496f9f82d146ee291333
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03962231

Reaction notes

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