Perchloric Acid → 7-(2-Methoxyimino-3-oxo-4-chlorobutyramido)-3-cephem-4-carboxylic acid

HRID 463432Notes

Reaction equation

HRID 463432 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][O:7][N:8]=[C:9]([C:25](OCC)([O:28]CC)[CH2:26][Cl:27])[C:10]([NH:12][CH:13]1[C:23](=[O:24])[N:15]2[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]12)=[O:11]>C(C(C)=O)C(C)C>[CH3:6][O:7][N:8]=[C:9]([C:25](=[O:28])[CH2:26][Cl:27])[C:10]([NH:12][CH:13]1[C:23](=[O:24])[N:15]2[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]12)=[O:11]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 131712536HCID 131712536, compound

Product 1

HCID 1317125357-(2-Methoxyimino-3-oxo-4-chlorobutyramido)-3-cephem-4-carboxylic acidYield 64.9%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

70% Perchloric acid (0.75 ml), 7-(2-methoxyimino-3,3-diethoxy-4-chlorobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 1.82 g) and methyl isobutyl ketone (7.3 ml) were treated in a similar manner to that of Example 47 to give 7-(2-methoxyimino-3-oxo-4-chlorobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 0.98 g).

Sources & evidence

ORD record
ord-e8a47fa6f095491a8049791718cf98ed
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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