Perchloric Acid → 7-(2-Methoxyimino-3-oxobutyramido)-3-hydroxycepham-4-carboxylic acid

HRID 1982031Notes

Reaction equation

HRID 1982031 reaction equation
Cl(O)(=O)(=O)=[O:2].[CH3:6][O:7][N:8]=[C:9]([C:26](=NNC(OCC)=O)[CH3:27])[C:10]([NH:12][CH:13]1[C:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[CH:17]([OH:20])[CH2:18][S:19][C@H:14]12)=[O:11]>CC(C)=O>[CH3:6][O:7][N:8]=[C:9]([C:26](=[O:2])[CH3:27])[C:10]([NH:12][CH:13]1[C:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[CH:17]([OH:20])[CH2:18][S:19][C@H:14]12)=[O:11]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 867380897-(2-Methoxyimino-3-ethoxycarbonylhydrazonobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 867380887-(2-Methoxyimino-3-oxobutyramido)-3-hydroxycepham-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

70% Aqueous perchloric acid (0.05 ml.) was added to a solution of 7-(2-methoxyimino-3-ethoxycarbonylhydrazonobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 40 mg.) in acetone (5 ml.), and stirred at room temperature for 30 minutes. The reaction mixture was treated in a similar manner to that of Example 10-(4) to give 7-(2-methoxyimino-3-oxobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 26 mg.).

Workup

  1. additionThe reaction mixture was treated in a similar manner to that of Example 10-(4)

Sources & evidence

ORD record
ord-95c4ef7f6fdb480b9768c72babdb63e8
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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