ChemicalBook CAS DataBase List Cefditoren pivoxil

Cefditoren pivoxil synthesis

10synthesis methods

Product Name:Cefditoren pivoxil
CAS Number:117467-28-4
Molecular formula:C25H28N6O7S3
Molecular Weight:620.72

Cefditoren Pivoxil is a semi-synthetic, broad-spectrum, beta-lactamase resistant, third-generation cephalosporin antibiotic with bactericidal activity. Cefditoren pivoxil is a prodrug that is rapidly hydrolyzed by intestinal esterases during absorption to the microbiologically active cefditoren, an active aminothiazolyl cephalosporin. Cefditoren inactivates penicillin binding proteins (PBPs) thereby interfering with peptidoglycan synthesis and inhibiting bacterial cell wall synthesis.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Sakagami, Kenji; Atsumi, Kunio; Yamamoto, Yuichi; Tamura, Atsuhi; Yoshida, Takashi; Nishihata, Ken; Fukatsu, Shunzo. Synthesis and oral activity of pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate (ME1207) and its related compound. Chemical & Pharmaceutical Bulletin. Pharm. Res. Cent. Meiji Seika Kaisha, Ltd. Yokohama, Japan 222. Volume 39. Issue 9. Pages 2433-6. 1991

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Yield:117467-28-4 98.75%

Reaction Conditions:

Stage #1: cefditorenwith pyridine in N,N-dimethyl-formamide at -10;
Stage #2: iodomethyl pivaloate at -10; for 1 h;

Steps:

9 Example 9: Preparation of Compound 1

Compound 2 (5.29 g, 10 mmol) and 60 mL of N,N-dimethylformamide were added to the reaction flask, and the mixture was stirred for 30 min.Cool down to 0 ° C or below 0 ° C,Add 8.5mmol of pyridine,Cool down to -10 ° C, join quickly20mmol iodomethyl pivalate,Insulation reaction for 1 h,Add activated carbon and stir for 30min, decolorization filtration,The filtrate was added with 5 g of anhydrous sodium sulfate.Add 30 mL of water and 60 mL of ethyl acetate.Stir, let stand,The aqueous phase was extracted once with ethyl acetate.Combine ethyl acetate,Evaporate the solvent under reduced pressure.Get oil,Add 10mL of acetone,40mL of isopropyl ether, crystallization, filtration,Drying cefoperapyl pure product 6.14g,The yield is 98.75%.The purity is 99.84%.

References:

CN109336904,2019,A Location in patent:Paragraph 0042; 0043

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