7-Aminocephalosporanic acid → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid
Reaction equation
C[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.C([O-])([O-])OC>[Cl-].[Zn+2].[Cl-].S1(CCCC1)(=O)=O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][O:4][CH3:2])[CH2:15][S:14][C@H:9]12Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To 10 ml of sulfolane were added 1.41 g of 7-ACA, 0.99 g of ferric chloride, 5.00 g of zinc chloride and 0.92 ml of methyl orthoformate. The mixture was heated at 50° C. for 6 hours to advance a reaction. After completion of the reaction, substantially the same procedure as in Example 1 was repeated, to thereby obtain a desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.81 g. The yield of the desired product was 64%.
Workup
- customa reaction
- customAfter completion of the reaction
Sources & evidence
- ORD record
- ord-cf59983465d441288db9be720e236272
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05034521
Reaction notes
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