89789-07-1Relevant articles and documents
2 β - Azidomethyl penicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam
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Paragraph 0039; 0041; 0045; 0048-0049, (2021/11/21)
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
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, (2021/11/21)
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.
Self-Assembled Polymeric Pyridine Copper Catalysts for Huisgen Cycloaddition with Alkynes and Acetylene Gas: Application in Synthesis of Tazobactam
Hu, Hao,Ohno, Aya,Sato, Takuma,Mase, Toshiaki,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
, p. 493 - 498 (2019/04/30)
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.