7-(2-Methoxyimino-3,3-ethylenedioxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid → 7-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

HRID 463417Notes

Reaction equation

HRID 463417 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:21]1(OCC[O:24]1)[CH2:22][Br:23])[C:5]([NH:7][CH:8]1[C:19](=[O:20])[N:10]2[CH:11]([C:16]([OH:18])=[O:17])[CH:12]([OH:15])[CH2:13][S:14][C@H:9]12)=[O:6]>C(O)(=O)C>[CH3:1][O:2][N:3]=[C:4]([C:21](=[O:24])[CH2:22][Br:23])[C:5]([NH:7][CH:8]1[C:19](=[O:20])[N:10]2[CH:11]([C:16]([OH:18])=[O:17])[CH:12]([OH:15])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

3

Reactant 1

HCID 867380907-(2-Methoxyimino-3,3-ethylenedioxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 867380917-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acidYield 66.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-[2-Methoxyimino-3,3-ethylenedioxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 1 g.), 70% aqueous hydroperchloric acid (0.2 ml.) and acetic acid (2 ml.) were treated in a similar manner to that of Example 10 (4) to give 7-[2-methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 0.6 g.).

Sources & evidence

ORD record
ord-63d2b7a61c134112bc86427d6a37f0b7
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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