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Synthesization technique for ceftibuten side chain

A ceftibuten side chain and synthesis process technology, applied in the direction of organic chemistry, can solve the problems of ceftibuten difficult to localize and process to industrialize, and achieve strong controllability, stable yield, and low yield Effect

Inactive Publication Date: 2012-02-22
HUANGSHAN SHEXIAN HONGHUI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The processes of the above two existing technologies are difficult to industrialize, making it difficult to localize ceftibuten

Method used

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  • Synthesization technique for ceftibuten side chain
  • Synthesization technique for ceftibuten side chain
  • Synthesization technique for ceftibuten side chain

Examples

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Embodiment Construction

[0029] The present invention will be further described below in conjunction with specific embodiment:

[0030] Carboxyl protection. Take a 5000mL dry three-neck flask, add anhydrous methanol (1600mL, solvent and reactant) and 2-aminothiazoleacetic acid (250g, 1.59mol) under mechanical stirring, add concentrated sulfuric acid (8g, 0.08mol) after stirring evenly, stir and heat up Return to reflux and maintain for 48 hours, recover about 1300mL of methanol by distillation under normal pressure, slowly cool to room temperature with stirring, add 400mL of ethyl acetate:petroleum ether=1:4 mixed solution, precipitate solids under stirring until complete, filter with suction, filter cake Wash with petroleum ether and dry to obtain off-white solid: methyl 2-aminothiazole acetate, 223 g in total. Crude yield: 82%. mp: 124-126°C. 1 H-NMR (CDCl 3 ): δ: 3.54(s, 2H), 3.68(s, 3H), 5.57(s, 2H), 6.29(s, 1H); 13 C-NMR (CDCl 3 ): δ: 37.6, 52.5, 104.0, 145.1, 169.1, 171.4.

[0031] Amino ...

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Abstract

The invention discloses a synthesization technique for a ceftibuten side chain. Adopting 2-aminothiazole acetic acid as starting material, the technique synthesizes a target compound, i.e. the ceftibuten side chain: (Z / E)-2-[2-[[( benzyloxy)formacyl]amino]-4-thiazolyl]-2-glutaconate-5-(3-methyl-2-butylene)ester by carboxyl group protection, amino group protection, hydroxymethylation, witing reaction and monoesterification. Since the invention does not use the expensive imported reagent, methyl 3-methoxyacrylate, the cost is reduced, and the invention solves the problem that industrialized material is difficultly obtained; because diphenyldiazomethane is not used, the two high-toxic and flammable chemical materials, i.e. yellow mercury oxide and diethyl ether, are not used; high-corrosive trifluoroacetic acid is not used for single hydrolysis, environment pollution is reduced, the operation of the technique is simple, controllability is high, the yield is high and stable, and the technique is suitable for industrialized production.

Description

technical field [0001] The present invention relates to a kind of synthetic technique of cephalosporin antibiotic key intermediate, relate in particular to a kind of synthetic technique of ceftibuten side chain, i.e. (Z / E)-2-[2-[[(benzyloxy)formyl ]Amino]-4-thiazolyl]-2-pentaconate-5-(3-methyl-2-butene) ester. Background technique [0002] Ceftibuten, English name Ceftibuten (other names are ceftibutan, 7432-5, etc.), is the third generation broad-spectrum oral cephalosporin created by Shionogi Company in Japan. The chemical name is 7β-[2-(2-amino-4-thiazolyl)-4-carboxy-2-(Z)-butenamido]-3-cephem-2-carboxylic acid. It was first listed in Japan under the trade name Seftem in 1992, and then transferred to Schering-Suiya Corporation worldwide except Japan and some other Asian countries. So far, it has been listed in more than 30 countries under the trade name Cedax ). It has two dosage forms, capsule (200mg / capsule, 400mg / capsule) and suspension (90mg / mL, 180mg / 5mL). This p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/18
Inventor 方维政张宏坚钱东勃
Owner HUANGSHAN SHEXIAN HONGHUI CHEM
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