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Method for electrochemical synthesis of tazobactam key intermediate

A tazobactam, electrochemical technology, applied in the field of electrochemical synthesis of key intermediates of tazobactam, can solve the problems of low reaction efficiency, low selectivity, poor economy and the like

Active Publication Date: 2021-07-06
JINLIN ASYMCHEM PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The main purpose of the present invention is to provide a method for electrochemically synthesizing the key intermediate of tazobactam, to solve the problem of low selectivity and reaction when synthesizing 2β-triazolemethyl penicillate in the prior art. Problems such as low efficiency or poor economy

Method used

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  • Method for electrochemical synthesis of tazobactam key intermediate
  • Method for electrochemical synthesis of tazobactam key intermediate
  • Method for electrochemical synthesis of tazobactam key intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1: Preparation 2β-triazole methylmirinate C

[0040]

[0041] At room temperature, a magneton was added to the non-separated electrolysis tank (8 mL), and a double sulfur-randoma A (133 mg, 0.25 mmol), 1,2,3-triazole B (138 mg, 2 mmol,) were added to the slot. 8EQ), tetrabutyate (185 mg, 0.5 mmol, 2 eq). Acetonitrile (4.5 mL) and acetic acid (0.5 ml) were added using a syringe. After all materials are added, the graphite sheet (1 × 7 × 0.3cm) is equipped. 3 ) And platinum tablet (1 × 7 × 0.3cm 3 ), Electrode immersion area is 2cm 2 (At this time, the current density is 4mA / cm 2 ). The reaction mixture was stirred for 10 min, and the DC power supply was adjusted to constant current mode, and 8 mA electrolysis 5f was completely converted. After the end of the reaction, the reaction liquid sampled from the HPLC external standard, the yield was 76.8%, and the column chromatography was separated to obtain a white solid, and the yield was 76.2%.

[0042] Nuclear magne...

Embodiment 2

[0043] Example 2: Carbon felt as an anode prepared 2β-triazole methylmidin-dibenzyl

[0044] At room temperature, a magneton was added to the non-separated electrolysis tank (8 mL), and a double sulfur-randoma A (133 mg, 0.25 mmol), 1,2,3-triazole B (138 mg, 2 mmol,) were added to the slot. 8EQ), tetrabutyate (185 mg, 0.5 mmol, 2 eq). Acetonitrile (4.5 mL) and acetic acid (0.5 ml) were added using a syringe. After all materials are added, equipment is equipped with carbon felt (1 × 7cm 2 ) And platinum tablet (1 × 7 × 0.3cm 3 As the yin and inferior, the electrode immersion area is 2 cm 2 . The reaction mixture was stirred for 10 min, and the DC power supply was adjusted to constant current mode, and 8 mA electrolysis 5f was completely converted. After the reaction, the reaction liquid was sampled from the HPLC external standard, and the yield was 71.0%.

Embodiment 3

[0045] Example 3: Tablet as a cathode Preparation 2β-triazol methylpatoenenenate C

[0046] At room temperature, a magneton was added to the non-separated electrolysis tank (8 mL), and a double sulfur-randoma A (133 mg, 0.25 mmol), 1,2,3-triazole B (138 mg, 2 mmol,) were added to the slot. 8EQ), tetrabutyate (185 mg, 0.5 mmol, 2 eq). Acetonitrile (4.5 mL) and acetic acid (0.5 ml) were added using a syringe. After all materials are added, the graphite sheet (1 × 7cm) is equipped. 2 ) And iron sheet (1 × 7 × 0.2cm 3 As the yin and inferior, the electrode immersion area is 2 cm 2 . The reaction mixture was stirred for 10 min, and the DC power supply was adjusted to constant current mode, and 8 mA electrolysis 5f was completely converted. After the reaction, the reaction liquid sampled the HPLC external standard, yield 49.2%.

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Abstract

The invention provides a method for electrochemical synthesis of a tazobactam key intermediate. The method comprises the following steps: by taking a disulfide ring-opening compound A and 1, 2, 3-triazole B as reaction substrates, mixing the reaction substrates, electrolyte and a reaction solvent, and then performing electrochemical anodic oxidation to obtain the tazobactam key intermediate C. The method effectively solves the problems of low selectivity, low reaction efficiency or poor economical efficiency and the like during synthesis of 2 beta-triazole methyl penicillic acid diphenylmethyl ester in the prior art.

Description

Technical field [0001] The present invention relates to the field of organic synthesis, and in particular, a method of electrochemically synthesizing the critical intermediate of the synthesis of ozazinezama. Background technique [0002] In 1940, penicillin was applied to clinical treatment. This β-lactam antibiotic has developed into ceftrians, and has played a very excellent role in anti-infection. The β-lactam antibiotics use inhibits penicillin binding protein to use treatment. effect. By studying the moisture effect relationship of Penicillone sulfone derivative, it can be modified at its 6-position or 2β-methyl base, and a more active β-lactam antibiotic can be obtained. Among them, the effect of tazobactam is best. Tazoliban can have an effective synergistic effect with a variety of beta-lactam antibiotics, increasing antibacterial activity and expanding its antibacterial spectrum. The compound preparation of tazobartan has a strong effect on abdominal cavity, respiratory...

Claims

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Application Information

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IPC IPC(8): C25B3/23C25B3/05C25B3/07C25B3/09C25D11/02
CPCC25D11/02Y02P20/55
Inventor 肖毅王攀张恩选刘志清孙丽杰
Owner JINLIN ASYMCHEM PHARM CO LTD
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