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ChemicalBook CAS DataBase List cefuracetime
39685-31-9

cefuracetime synthesis

2synthesis methods
-

Yield: 90%

Reaction Conditions:

Stage #1:furan-2-yl-oxo-acetaldehyde;7-Aminocephalosporanic acid with tert.-butylhydroperoxide;C8H19Cl2OPPd in 2-methyltetrahydrofuran at 45; for 2.5 h;Sealed tube;Inert atmosphere;
Stage #2:O-Methylhydroxylamin with Trimethylacetic acid in 2-methyltetrahydrofuran;water at 45; for 2.5 h;Sealed tube;Inert atmosphere;Reagent/catalyst;Solvent;Temperature;

Steps:

1-5 Example 1
In a 25mL reaction vessel, put the weighed PdCl2[(tBu)2P(OH)](5.0%mol) into it, seal it, and replace it with nitrogen 3 times; then, the 2-(2-furanyl)-2 -Oxo-acetaldehyde (1.2equiv.) and 7-aminocephalosporanic acid (0.2mmol, 1.0equiv.) were dissolved in 2-methyltetrahydrofuran (0.1M) except for the water, and then the solution was pumped into a sealed airtight Put the weighed tert-butanol peroxide (2.0equiv.) into the reaction vessel; stir well and react at 45 for 2.5 hours; then, put the weighed pivalic acid (5.0% mol) Put it into the reaction vessel, keep the temperature at 45°C, and then slowly drop the weighed 40%wt methoxyamine (2.0euqiv.) aqueous solution into the closed reaction vessel drop by drop for 2.5 hours; The residue of 7-aminosporanic acid was detected by high performance liquid chromatography. After the detection reaction, the system was cooled to room temperature; the organic phase was washed and extracted, and the target product was obtained by flash column chromatography. The stationary phase of the chromatography column It is silica gel, the mobile phase is a mixed solution of water and acetonitrile, and finally a white slurry of 3-decarbamoyl-acetyl-cefuroxime compound (90% wt) is obtained.

References:

CN112679527, 2021, A Location in patent:Paragraph 0038-0048

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