Preparation method of 3-ethyl-4-7-aminocephalosporanic acid

A technology of cephalosporanic acid and vinyl, which is applied in the field of preparing 7-amino-3-vinyl-4-cephalosporanic acid, can solve the problems of low equipment requirements, low production cost, high raw material cost, etc., and achieve short reaction route, The effect of less three wastes and low cost of raw materials

Active Publication Date: 2015-12-09
山东昌邑四方医药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using 7-ACA or acetyl cephalosporin C as the raw material, the synthetic route is short and the equipment requirements are low, but the raw material cost is high; the raw material is penicillin potassium salt, the price is cheap, and the production of penicillin in my country is relatively large

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0021] Example 1: Preparation of 7-amino-3-vinyl-4-cephalosporanic acid

[0022] In a 50 ml three-necked flask, add 46 mg (0.1 mmol) of p-methoxybenzyl 7-phenylacetamido-3-vinyl-4-cephalosporanic acid, solid super acid catalyst S 2 O 8 2- / SnO 2 -Fe 2 O 3 23mg, 46mg of dichloromethane, 46mg of isoamyl acetate, 138mg of acetonitrile, react at 5°C for 5 hours, then cool the reaction solution to room temperature, then add 10mg of activated carbon to the reaction solution for decolorization, filter, and concentrate the filtrate to precipitate a pale yellow Solid 18.3mg, yield 81%. m.p.180~182℃, purity ≥96%.

[0023] IR(KBr)cm -1 : 3158,3010,2890,1800,1615,1540,1060.

[0024] 1 H-NMR(D 2 O,400MHz)δ:3.52~3.67(2H,ABq,C 2 H 2 ),5.02~5.05(1H,dd,C 6 -H), 5.19~5.20(1H,dd,C 7 -H), 5.34~5.37 (1H, d, Vinyl-H), 5.38~5.40 (1H, d, Vinyl-H), 6.68~6.72 (1H, dd, Vinyl-H).

Example Embodiment

[0025] Example 2: Preparation of 7-amino-3-vinyl-4-cephalosporanic acid

[0026] In a 50 ml three-necked flask, add 46 mg (0.1 mmol) of p-methoxybenzyl 7-phenylacetamido-3-vinyl-4-cephalosporanic acid, solid super acid catalyst S 2 O 8 2- / SnO 2 -Fe 2 O 3 46mg, methylene chloride 46mg, isoamyl acetate 92mg, acetonitrile 230mg, react for 10 hours at 0°C, then cool the reaction solution to room temperature, then add 10mg activated carbon to the reaction solution for decolorization, filter, and concentrate the filtrate to precipitate a pale yellow The solid was 18.5 mg, and the yield was 82%. m.p.180~182℃, purity ≥96%.

Example Embodiment

[0027] Example 3: Preparation of 7-amino-3-vinyl-4-cephalosporanic acid

[0028] In a 50 ml three-necked flask, add 46 mg (0.1 mmol) of p-methoxybenzyl 7-phenylacetamido-3-vinyl-4-cephalosporanic acid, solid super acid catalyst SO 4 2- / SnO 2 -Fe 2 O 3 46mg, 46mg of dichloromethane, 138mg of butyl acetate, 230mg of acetonitrile, reacted at 0℃ for 10 hours, then the reaction solution was cooled to room temperature, and then 10mg of activated carbon was added to the reaction solution for decolorization, filtered, and the filtrate was concentrated to precipitate a pale yellow solid 18.2mg, yield 80.6%. m.p.180~182℃, purity ≥96%.

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Abstract

The invention discloses a preparation method of 3-ethyl-4-7-aminocephalosporanic acid. The method comprises the following steps: taking 7-(phenylacetyl) amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester as a raw material, taking solid superacid as a catalyst, reacting for 1 to 10 hours in mixed solvent of haloalkane, acetate and acetonitrile at the temperature of 0 to 50 DEG C, cooling a reaction solution to the room temperature, then processing to obtain faint-yellow solid and to obtain a target product, wherein solid superacid is a tin-series solid superacid modified by transitional metal; haloalkane is alkyl chloride with a carbon atomic number of 1 to 10; the acetate is CH3COOR, wherein R is alkane with a carbon atomic number of 1 to 10. By adopting a heterogeneous catalytic one-pot reaction technology and solid acid catalyst with high activity to prepare 7-(phenylacetyl) amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester, the technology is easy to operate, does not corrode equipment, has less waste water, waste gas and waste solid, is convenient in post-treatment and capable of reutilizing solid acid, and is an economical and practical environment-friendly technology.

Description

technical field [0001] The present invention relates to a new method for preparing 7-amino-3-vinyl-4-cephalosporanic acid. Background technique [0002] 7-Amino-3-vinyl-4-cephalosporanic acid (7-AVCA) is an important intermediate in the synthesis of the third-generation oral cephalosporin antibiotics Cefixime and Cefdinir. Cefixime has the characteristics of broad antibacterial spectrum, long half-life, less cross-resistance, less amount, and outstanding penetration performance; cefdinir is highly stable to β-lactamase, has broad antibacterial activity, high antibacterial activity, low toxicity, and adverse reactions Small. The patent protection of cefixime in our country ended in July 2001, and it has now expired. It is a pharmaceutical raw material urgently needed to be developed in our country; cefdinir was approved to go on the market in China in 2001. The administrative protection period ends in July 2006. Cefdinir and cefixime are cephalosporins currently recommende...

Claims

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Application Information

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IPC IPC(8): C07D501/18C07D501/04
CPCY02P20/584C07D501/18C07D501/04
Inventor 顾士崇裴文孙会
Owner 山东昌邑四方医药化工有限公司
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