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Synthetic method of ceftezol drug intermediate 2-(1H-1-tetrazolyl)acetic acid

A technology of demetazoline cephalosporin and synthetic method, which is applied in the field of synthesis of 2-acetic acid, a drug intermediate of demetazoline cephalosporin, can solve the problems of poor antibacterial effect and poor antibacterial effect of Acinetobacter, and achieve The effect of reducing intermediate links, reducing reaction temperature and reaction time, and increasing reaction yield

Inactive Publication Date: 2016-04-20
CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

They also have certain antibacterial activity against Proteus and Aerobacter aerogenes, which have poor antibacterial effects of the first-generation cephalosporins, and have poor antibacterial activity against Acinetobacter

Method used

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  • Synthetic method of ceftezol drug intermediate 2-(1H-1-tetrazolyl)acetic acid

Examples

Experimental program
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Effect test

example 1

[0011] (i) Add 0.51mol of 2-(5-nitro-1H-1-tetrazolyl)acetic acid (2) into the reaction vessel, the mass fraction is 0.56mol of 65% o-bromophenol solution (3), and the stirring speed is controlled at 130rpm , add cuprous chloride 0.26mol, mass fraction is 15% potassium chloride solution 310ml, control the solution temperature at 10°C, react for 7h, lower the solution temperature to 5°C, add mass fraction of 35% ammonium nitrite solution to adjust pH maintenance At 6, extract 5 times with mass fraction of 50% dimethyl sulfoxide, combine organic layers, wash with mass fraction of 60% cyclohexanol, dehydrate phosphorus pentoxide, evaporate dimethyl sulfoxide under reduced pressure, and add the residue to The mass fraction is 70% N-methylformamide, a solid is precipitated, filtered, and recrystallized in 95% acetamide to obtain 45.04 g of crystalline 2-(1H-1-tetrazolyl)acetic acid, with a yield of 69% .

example 2

[0013] Add 0.51mol of 2-(5-nitro-1H-1-tetrazolyl) acetic acid (2) in the reaction vessel, the mass fraction is 67% o-bromophenol solution (3) 0.58mol, control the stirring speed at 140rpm, add chlorine Cuprous chloride 0.26mol, mass fraction is 17% potassium chloride solution 310ml, control the solution temperature at 12°C, react for 8h, lower the solution temperature to 7°C, add mass fraction of 37% ammonium nitrite solution to adjust the pH to maintain at 6, Extract 6 times with 52% dimethyl sulfoxide in mass fraction, combine the organic layers, wash with 63% cyclohexanol in mass fraction, dehydrate with solid sodium hydroxide, evaporate dimethyl sulfoxide under reduced pressure, and add the residue to 72% N-methylformamide, a solid was precipitated, filtered, and recrystallized in 96% acetamide by mass fraction to obtain 47.65 g of crystalline 2-(1H-1-tetrazolyl)acetic acid with a yield of 73%.

example 3

[0015] Add 0.51mol of 2-(5-nitro-1H-1-tetrazolyl) acetic acid (2) in the reaction vessel, the mass fraction is 0.59mol of 70% o-bromophenol solution (3), control the stirring speed at 150rpm, add chlorine Cuprous chloride 0.26mol, mass fraction is 20% potassium chloride solution 310ml, control the solution temperature at 15°C, react for 9h, lower the solution temperature to 8°C, add mass fraction of 40% ammonium nitrite solution to adjust the pH to maintain at 7, Extract 7 times with 55% dimethyl sulfoxide, combine the organic layers, wash with 65% cyclohexanol, dehydrate phosphorus pentoxide, evaporate dimethyl sulfoxide under reduced pressure, and add the residue to 75% N-methylformamide, a solid was precipitated, filtered, and recrystallized in 98% acetamide to obtain 53.53 g of crystalline 2-(1H-1-tetrazolyl)acetic acid, with a yield of 82%.

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Abstract

Provided is a synthetic method of a ceftezol drug intermediate 2-(1H-1-tetrazolyl)acetic acid. The method comprises the following steps that 0.51 mol of 2-(5-nitryl-1H-1-tetrazolyl)acetic acid and 0.56-0.59 mol of o-bromophenol solution are added into a reaction vessel, and the stirring speed is controlled to range from 130 rpm to 150 rpm; 0.26 mol of cuprous chloride and 310 ml of potassium chloride solution are added, the temperature of the solution is controlled to range from 10 DEG C to 15 DEG C, a reaction is conducted for 7-9 h, the temperature of the solution is decreased to 5-8 DEG C, an ammonium nitrite solution is added to adjust the pH, the pH is maintained to range from 6 to 7, extraction is conducted for 5-7 times with dimethyl sulfoxide, organic layers are merged, cyclohexanol washing is conducted, dehydration is conducted through a dehydrating agent, reduced pressure distillation is conducted to distill off dimethyl sulfoxide, residues are added to N-methylformamide, a solid is precipitated, filtration is conducted, recrystallization is conducted in acetamide, and the crystalline 2-(1H-1-tetrazolyl)acetic acid is obtained.

Description

technical field [0001] The invention relates to a method for synthesizing 2-(1H-1-tetrazolyl)acetic acid, a drug intermediate of demetazoline cephalosporin. Background technique [0002] Demetazoline cephalosporin drugs have a broad antibacterial spectrum and are highly effective against anaerobic bacteria; the allergic reactions caused by them are lower than those of penicillins; they are more stable against acids and β-lactamase produced by various bacteria; their mechanism of action is the same as that of penicillins, It also inhibits the formation of bacterial cell walls to achieve the purpose of sterilization. It is a fungicide during breeding season. Because of its low adverse reactions and side effects, it is a class of antibiotics that are currently being developed rapidly. It can also bind to certain proteins (β-lactam-binding proteins), which may be some enzymes on the cell membrane in essence. This changes the permeability of the bacterial cell membrane, inhibi...

Claims

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Application Information

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IPC IPC(8): C07D257/04
CPCC07D257/04
Inventor 关艮安
Owner CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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