89789-07-1

Usage

Uses

Used in Antibiotic Therapy:
Tazobactam Diphenylmethyl Ester is used as a beta-lactamase inhibitor for enhancing the efficacy of antibiotics. It is often combined with piperacillin, an antibiotic that works by stopping the growth of bacteria, to broaden the spectrum of bacterial strains that can be effectively treated.
Used in Medical Research:
Tazobactam Diphenylmethyl Ester is used as a research compound for studying the interactions between antibiotics and bacterial enzymes, as well as for developing new strategies to combat antibiotic resistance. Its role in medical research is significant, although detailed information on its physical properties, uses, and health effects may not be readily available due to its specialized application.

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 74-86-2 acetylene 
• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 80353-26-0 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide 
• 551-16-6 6-Aminopenicillanic Acid 
• 24138-28-1 6-bromopenicillanic acid 
• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 
• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 
• 288-36-8 1,2,3-triazole 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 
• 85573-73-5 2β-(chloro)methyl-2α-methyl-6,6-dihydropenam-3α-carboxylic acid benzhydryl ester 

Downstream Products

• 89786-04-9 tazobactam acid 
• 89785-84-2 tazobactam sodium 

Relevant academic research and scientific papers

2 β - Azidomethyl penicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam

The invention provides a preparation method of 2 β -azipenicillanic acid dibenzoate, tazobactam intermediate and tazobactam. The preparation method comprises the following steps: carrying out free radical reaction in a solvent by using a reaction raw material comprising a double-sulfur open-loop compound, a stacked nitrogen source and an oxidant to obtain a product system comprising 2 β - azidomethyl penicillanic acid dibenzoate. By radical addition of the carbon-carbon double bonds of the double-sulfur ring-opening compound through the azide free radical, high-efficiency and high-selectivity synthesis of the disulphide ring-opening compound directly to 2 β - azimaapenem naphthenate is successfully realized through intramolecular radical substitution. Further, 2 β - azidomethyl penicillanic acid dibenzoate is taken as a key intermediate for synthesizing tazobactam, the yield of tazobactam is improved, and the cost is reduced.

Application of Continuous Flow in Tazobactam Synthesis

Tazobactam is a β-lactamase inhibitor. In this work, a combination of continuous flow and batch experiments for the synthesis of tazobactam has been developed. The first three steps and the preparation of the peroxyacetic acid are continuously carried out in the microreactors, which improves the procedure safety and efficiency. There is also a final step of the deprotection reaction in the microreactor, which can increase the yield and reduce the formation of impurities. Under optimized process conditions, the total yield of the target product reached 37.09% (30.93% in batch). The continuous flow method not only greatly reduces the reaction time but also significantly improves procedure safety and increases the yield.

2 β -triazole methylpenicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam

The invention provides a preparation method of 2 β -triazole methyl penicillanic acid dibenzoate, tazobactam intermediate and tazobactam. The preparation method comprises the following steps: reacting a reaction raw material comprising a double-sulfur ring opening compound, 1, 2, 3 - triazole and first oxidizing agent in first solvent to obtain a product system comprising 2 β - triazole methylpenicillanic acid dibenzoate. The structural formula of 2 β -triazole methylpenicillanic acid dibenzoate is shown. Under the action first oxidizing agent 1, 2 and 3 - triazole are used for directly closing the bicyclic ring opening compound, and the efficient and high-selectivity synthesis of the bis-sulfur ring-opening compound directly to the key intermediate 2 β - triazole methylpenicillanic acid dibenzoate is successfully realized. Further, 2 β - triazole methyl penicillanic acid dibenzoate is used as a key intermediate for synthesizing tazobactam, the yield of tazobactam is improved, and the cost is reduced.

Tazobactam intermediate, preparation method thereof and method for preparing tazobactam by using intermediate (by machine translation)

The intermediate V is prepared from glyoxal and hydrazine through dihydrazone of glyoxal, 1 - 2-triazole, and then reacted with (2S, 3S) 3 methyl -3 -methyl-3 -oxo -7 -thio -4 -methylpyridine-1 -thioxazabicyclo [3.2.0 -2 -] heptanoic acid to obtain an intermediate VII, and an intermediate VII is subjected to deprotection reaction to prepare the tazobarbazobactam intermediate V; the intermediate V is subjected to diazotization reaction to prepare the intermediate V. The preparation method of tazobactam is mild in reaction condition, simple in process, low in cost, high 90% in yield, high 99.0% in purity, environmentally friendly, good in economic benefit and suitable for industrial production. (by machine translation)

Preparation method of tazobactam

The invention discloses a preparation method of tazobactam. The preparation method comprises the following steps: performing double oxidization on 2beta-chloromethyl penicillanic acid diphenyl methylester by adopting a solution prepared from potassium permanganate, glacial acetic acid and concentrated sulfuric acid; then loading triazole by taking crown ether as a phase transfer catalyst and taking potassium iodide as a catalyst; then performing deprotection to obtain tazobactam. Compared with the prior art, the preparation method disclosed by the invention has the advantages that although sulfur atoms are oxidized into sulfone to lower chlorine atom activity, the use of the crown ether as the phase transfer catalyst and the potassium iodide as the catalyst compensates for the inactivation well. By adopting the method, the stability of the 2beta-chloromethyl penicillanic acid diphenyl methyl ester is improved, the reaction time is shortened, the reaction yield is improved, the operation risk is lowered, and the industrial production is facilitated.

Self-Assembled Polymeric Pyridine Copper Catalysts for Huisgen Cycloaddition with Alkynes and Acetylene Gas: Application in Synthesis of Tazobactam

Novel convoluted polymeric pyridine copper(I) catalysts PVPy-Cu were developed for the Huisgen cyclization of organic azides using alkynes and acetylene gas. They were readily prepared based on our molecular convolution of CuSO4·5H2O and poly(4-vinylpyridine) (PVPy) in the presence of sodium ascorbate with and without various sodium salts in water. Their structural investigation was conducted using XANES and EXAFS, as well as DFT calculation. The Huisgen cycloaddition of a variety of alkynes and acetylene gas was carried out using 100 to 800 mol ppm of Cu of PVPy-Cu in water, whose turnover numbers reached up to 10 000. This catalytic system was applied to the synthesis of tazobactam, which is an inhibitor of bacterial β-lactamases.

Preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application

The invention relates to preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application. A preparation route is as follows: with methylbenzene, 2-mercaptobenzothiazoleand a debrominated product as starting materials, the tazobactam diphenylmethyl ester is prepared after a ring opening reaction, a chlorination reaction, a condensation reaction and a double oxidation reaction, then the tazobactam diphenylmethyl ester is transformed into the tazobactam acid after a deprotection reaction; a preparation method in the scheme is improved on the basis of an iodinationreaction in the prior art, and the chlorination reaction is introduced, so that the reaction quality is optimized, the product purity is improved, and use of toxic, harmful, flammable and explosive substances in the reaction process is reduced, and thus the reaction is more environment-friendly; the product yield can be as high as 98-99.92%, and the preparation cost is also lower than that of thepreparation technology in the prior art.

Synthetic method of tazobactam diphenylmethyl ester

The invention provides a synthetic method of tazobactam diphenylmethyl ester. The synthetic method comprises the following step: under the action of a catalyst, a compound A and hydrogen peroxide aresubjected to an oxidation reaction to obtain the tazobactam diphenylmethyl ester (the synthetic route is as follows). In the synthetic method provided by the application, the hydrogen peroxide is usedas an oxidant, and the only by-product is water, so that on the one hand, the generation of waste solids can be greatly reduced, the amount of three wastes is greatly reduced, and the environment-friendly performance of the process is improved, and on the other hand, since the reaction by-product is only water, the synthetic method is adopted to facilitate improvement of the purity of a tazobactam diphenylmethyl ester product. Besides, the synthetic method has the advantages that the purity of the product can reach 98%, the post-treatment operation is simple, the separation yield is as high as 95.7%, and amplified production is easy.

A he zuozuo batanbatan benzoin methyl ester

The invention discloses a synthesis method of tazobactam diphenylmethyl ester. The method comprises the following steps: reacting 1-H-1,2,3-triazole with NaOH or KOH, purifying, and crystallizing to obtain a crystal sodium 1,2,3-triazole or potassium 1,2,

Synthetic method of tazobactam acid

The invention provides a synthetic method of tazobactam acid, comprising the steps of (a) using 6-APA (6-aminopenicillanic acid) as a starting material and cetyltrimethylammonium hydrogensulfate as a catalyst to oxidize with oxone to obtain compound A; subjecting the compound A to deamination reaction to obtain compound B; esterifying the compound B to obtain compound C; (b) subjecting the compound C and 2-mercaptobenzothiazole to reduced pressure backflow to obtain compound D; ultrasonically vibrating the compound D and copper bromide to obtain compound E; reacting the compound E and 1H-1,2,3-triazole to obtain compound F; (c) allowing hydrogen peroxide and acetic anhydride to act on the compound F to obtain compound G; reacting the compound G with anisole to obtain tazobactam acid. Amino groups in 6-APA are diazotized directly, diazo groups are then removed, reduced pressure backflow and ultrasonic vibration are performed, hydrogen peroxide and acetic anhydride are used as oxidants, less byproducts are generated, and the yield and quality of tazobactam acid are effectively increased.