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Preparation method of ethyl 2-[[(bezyloxy)carbonyl]amido]-4-thiazolyl acetate

A technology of thiazolyl acetate and benzyloxy, applied in the field of pharmaceutical intermediates, can solve problems such as increased difficulty, high cost, unrealistic industrialized production, etc., and achieves the effects of easy operation, few reaction procedures, and reduced production costs

Inactive Publication Date: 2009-02-11
SHANDONG JINCHENG PHARMA & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs to use a large excess (2.5 times) of benzyl chloroformate to react with ethyl aminothiazole acetate, the cost is higher, and the difficulty of post-treatment is correspondingly improved, so it is not realistic to be applied to industrialized production

Method used

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  • Preparation method of ethyl 2-[[(bezyloxy)carbonyl]amido]-4-thiazolyl acetate
  • Preparation method of ethyl 2-[[(bezyloxy)carbonyl]amido]-4-thiazolyl acetate
  • Preparation method of ethyl 2-[[(bezyloxy)carbonyl]amido]-4-thiazolyl acetate

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1 Preparation of ethyl 2-[[(benzyloxy)carbonyl]amino]-4-thiazolyl acetate

[0024] In a 500ml reaction flask, add 200g ethanol, 0.5g (4mmol) 4-dimethylaminopyridine, 8.3g (105mmol) pyridine and stir, cool to -5°C, add 17.9g (105mmol) benzyl chloroformate, continue React for 2h, then warm up to 10°C, react for 8h, and filter. The filtrate was put into 18.6g (100mmol) ethyl 2-amino-4-thiazolyl acetate, stirred and reacted at this temperature for 18h to obtain 14.2g of 2-[[(benzyloxy)carbonyl]amino]-4-thiazolyl Ethyl acetate, yield 44.4% (calculated as ethyl 2-amino-4-thiazolyl acetate).

Embodiment 22-

[0025] Preparation of Example 22-[[(Benzyloxy)carbonyl]amino]-4-thiazolylacetic acid methyl ester

[0026] In a 500ml reaction flask, add 86g methanol, 1.2g (10mmol) 4-dimethylaminopyridine, 10.1g (100mmol) triethylamine and stir, cool down to -10°C, add 17.1g (100mmol) benzyl chloroformate , Continue to react for 2h, then raise the temperature to 15°C for 6h, and filter. The filtrate was put into 17.2g (100mmol) 2-amino-4-thiazolyl acetate, and stirred at this temperature for 18h to obtain 10.7g of 2-[[(benzyloxy)carbonyl]amino]-4-thiazolyl Methyl acetate, yield 35.0% (calculated as methyl 2-amino-4-thiazolyl acetate).

Embodiment 32-

[0027] Example 32- Preparation of ethyl [[(benzyloxy)carbonyl]amino]-4-thiazolyl acetate

[0028] In a 500ml reaction flask, add 280g isopropanol, 0.1g (1mmol) 4-dimethylaminopyridine, 15.9g (150mmol) Na 2 CO 3 Stir, cool down to 0°C, add 25.6 (150 mmol) benzyl chloroformate, continue the reaction for 1 hour, then raise the temperature to 15°C for 4 hours, and filter. The filtrate was put into 18.6g (100mmol) ethyl 2-amino-4-thiazolyl acetate, stirred and reacted at this temperature for 12h to obtain 10.4g of 2-[[(benzyloxy)carbonyl]amino]-4-thiazolyl Ethyl acetate, yield 32.7% (calculated as ethyl 2-amino-4-thiazolyl acetate).

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Abstract

The invention discloses a method for preparing 2[[(benzyloxy) carbonyl] amino]-4-thiazolyl acetate. In the method, alcohol is used as a reactant and a solvent; 1.0mol to 1.5mol of benzyl chloroformate and equal molar weight of alkaline are added in; 0.01mol to 0.10mol of 4-dimethylaminopyridine is used as a catalyst for reaction at -10 DEG C to 0 DEG C for 1h to 2h; the temperature is increased to 0 DEG C to 15 DEG C for 4h to 10h and filtration is carried out; the filtrate is added with 1.0mol of 2-amino-4-thiazolyl acetate for further reaction for 12h to 24h at the same temperature, and then the 2(((benzyloxy) carbonyl) amino)-4-thiazolyl acetate is produced. The method for preparing the 2(((benzyloxy) carbonyl) amino)-4-thiazolyl acetate has few reaction processes, low cost, simple operation, few 'three wastes'(waste gas, waste water and waste residues) and is in favor of industrialized production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical intermediates, and relates to a method for preparing an intermediate of cephalosporin antibiotics, in particular to a method for preparing 2-[[(benzyloxy)carbonyl]amino]-4-thiazolyl acetate . Background technique [0002] 2-[[(Benzyloxy)carbonyl]amino]-4-thiazolyl acetate is a white crystalline powder, easily soluble in dichloromethane, chloroform and other organic solvents, slightly soluble in methanol, ethyl acetate, Solvents such as acetone. It is mainly used as a raw material for the synthesis of ceftibuten, and its molecular structure is as follows: [0003] [0004] Where R is methyl, ethyl, etc. [0005] J.Chem.Soc., 1948, page 2240 describes the preparation of 2-[[(benzyloxy)carbonyl]amino]-4 in an organic solvent with ethyl thiazole acetate as raw material. - ethyl thiazolyl acetate. This method uses pyridine as an acid-binding agent, which has many steps and high cost. Even if the t...

Claims

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Application Information

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IPC IPC(8): C07D277/48
Inventor 张学波尹鹏刘刚徐立臣
Owner SHANDONG JINCHENG PHARMA & CHEM
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