85573-73-5

Usage

Uses

Used in Pharmaceutical Industry:
(2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester is used as an intermediate in the synthesis of Tazobactam Sodium Salt-15N3 (T010103), a β-lactamase inhibitor. This inhibitor is used in combination with β-lactam antibiotics to enhance their effectiveness against bacterial infections. By inhibiting the β-lactamase enzymes produced by bacteria, Tazobactam Sodium Salt-15N3 helps to prevent the degradation of β-lactam antibiotics, allowing them to exert their antibacterial action more effectively.

Upstream product

• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 
• 551-16-6 6-aminopenicillanic acid 
• 205320-23-6 benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide 
• 80353-26-0 Benzhydryl 6α-bromopenicillanate-1-oxide 
• 205320-26-9 6α-Bromopenicillanic acid 
• 85573-72-4 2-oxo-4-(benzothiazol-2-yl)dithio-α-isopropenyl-1-azetidine acetic acid benzhydryl ester 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 
• 73968-83-9 benzhydryl 6,6-dihydropenicillate 
• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 

Downstream Products

• 122661-93-2 2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester 
• 89786-04-9 tazobactam acid 
• 89789-07-1 (2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester 
• 1379595-05-7 C₂₆H₂₈N₃O₅S⁽¹⁺⁾*I^(1-) 
• 1379595-04-6 (2S,3S,5R)-3-(4-methyl-iinidazol-1-ylmethyl)-3-methyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 

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.

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.

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.

PENICILLIN CRYSTAL AND PROCESS FOR PRODUCING THE SAME

The present invention provides 2β-chloromethyl-2α-methylpenam-3α-carboxylic acid benzhydryl ester (CMPB) crystals of excellent stability, and a process for producing the CMPB crystals comprising the steps of (A) concentrating a solution containing CMPB; (

Synthesis of penicillin derivatives and study of their cytotoxic properties

By the interaction of heterocyclic thiols with sulforides of 6,6-dihydro- and 6α-chloropenicillanates, derivatives of 4-heteryldithio-2-azetidinones have been synthesized, as well as products of their cyclization to form 2β-heterylthiomethyl-and 2β-halorn