Acetic Acid → 7-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-methylenecepham-4-carboxylic acid
Reaction equation
C(O)(=O)C.[CH3:5][O:6][N:7]=[C:8]([C:35]1([O:40][CH2:39][CH2:38][O:37]1)[CH3:36])[C:9]([NH:11][CH:12]1[C:33](=[O:34])[N:14]2[C:15]([C:30]([OH:32])=[O:31])=[C:16]([CH2:19]SC3SC4C=CC=CC=4N=3)[CH2:17][S:18][C@H:13]12)=[O:10].CON=C(C1(OCCO1)C)C(NC1C(=O)N2C(C(O)=O)=C(C)CS[C@H]12)=O>O1CCCC1.O.[Zn]>[CH3:5][O:6][N:7]=[C:8]([C:35]1([O:40][CH2:39][CH2:38][O:37]1)[CH3:36])[C:9]([NH:11][CH:12]1[C:33](=[O:34])[N:14]2[CH:15]([C:30]([OH:32])=[O:31])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12)=[O:10]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
Acetic acid (1 ml.) was added to a solution of 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-(benzothiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 500 mg.) in tetrahydrofuran (6 ml.) and water (2 ml.). Zinc powder (500 mg.) and copper sulfate 5-hydrate (50 mg.) were added to the solution at room temperature, and stirred at the same temperature for 2 hours. The resultant mixture was treated in a similar manner to that of Example 10-(3) Method A to give a mixture (120 mg.) of 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-methylenecepham-4-carboxylic acid (syn isomer) and 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-methyl-3-cephem-4-carboxylic acid (syn isomer) (5:1).
Sources & evidence
- ORD record
- ord-47c2a824205947ff92ad118e1c03ce90
- Source dataset
- uspto-grants-1981_11
- Patent number
- US04298529
Reaction notes
Loading…