89789-07-1

Basic information

• Product Name: Tazobactam Diphenylmethyl Ester
• Synonyms: Tazobactam Diphenylmethyl Ester;Benzhydry 2β-triazolmethyl-2α-methyl-6,6-dihydropernicillanate-1,1-dioxide;Benzhydry 2beta-triazolmethyl-2alpha-methyl-6,6-dihydropernicillanate-1,1-dioxide;(2S,3S,5R)-3-METHYL-7-OXO-3-(1H-1,2,3-TRIAZOLE-1-YLMETHYL)-4 - -THIA-1-AZABICYCLO(3.2.0)-HEPTANE-2-CARBOXYLIC ACID DIPHENYL
• CAS NO: 89789-07-1
• Molecular Formula: C₂₃H₂₂N₄O₅S
• Molecular Weight: 466.516
• EINECS: 1312995-182-4
• Mol File: 89789-07-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 717.5±70.0 °C(Predicted)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• PKA: 0.85±0.12(Predicted)
• CAS DataBase Reference: Tazobactam Diphenylmethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: Tazobactam Diphenylmethyl Ester(89789-07-1)
• EPA Substance Registry System: Tazobactam Diphenylmethyl Ester(89789-07-1)

Safety Data

• Hazardous Substances Data: 89789-07-1(Hazardous Substances Data)

Usage

General Description

Tazobactam Diphenylmethyl Ester is a derivative of Tazobactam, a pharmaceutical drug that serves as a potent beta-lactamase inhibitor used in combination with other antibiotics to broaden their spectrum of efficacy. The main function of Tazobactam Diphenylmethyl Ester is to protect the antibiotic drug from deactivation by bacterial enzymes called beta-lactamases, thereby enhancing the antibiotic's ability to kill bacteria. It is often used in combination with piperacillin, an antibiotic that works by stopping the growth of bacteria. However, detailed information related to its physical properties, uses, and health effects is not easily accessible, possibly due to its specific role in medical research rather than general usage.

Upstream product

• 24138-28-1 6-bromopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 
• 80353-26-0 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide 
• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 74-86-2 acetylene 
• 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 
• 85573-73-5 2β-(chloro)methyl-2α-methyl-6,6-dihydropenam-3α-carboxylic acid benzhydryl ester 
• 73968-83-9 benzhydryl 6,6-dihydropenicillate 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 

Downstream Products

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

Relevant articles and documents

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.

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.

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.