Catalytic oxidation system and use thereof in tazobactam synthesis

A catalytic oxidation and system technology, applied in the field of chemistry, can solve the problems of high price of hexafluoroisopropanol, difficult recovery and high volatility, and achieve the effects of high utilization rate, good reaction selectivity and mild reaction conditions

Active Publication Date: 2009-05-20
山东安信制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ravikumar, K.S reported that the hydrogen peroxide / hexafluoroisopropanol method can efficiently oxidize general sulfides into sulfoxides, but hexafluoroisopropanol is expensive, too toxic, and has a low boiling point, high volatility, and difficult recovery

Method used

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  • Catalytic oxidation system and use thereof in tazobactam synthesis
  • Catalytic oxidation system and use thereof in tazobactam synthesis

Examples

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Effect test

Embodiment 1

[0033] Embodiment 1. Preparation of catalytic oxidation system

[0034] Catalytic oxidation system of sodium tungstate, hydrochloric acid and hydrogen peroxide

[0035] Sodium tungstate and 30% hydrogen peroxide were mixed at a mass ratio of 1.5:100, stirred for 5-10 minutes, and the pH was adjusted to 2.0 with about 1ml of 16% hydrochloric acid. At this point the color of the solution is pale yellow or just disappears.

Embodiment 2

[0036] Embodiment 2. Preparation of catalytic oxidation system

[0037] Catalytic Oxidation System of Sodium Tungstate, Oxalic Acid and Hydrogen Peroxide

[0038] Sodium tungstate, oxalic acid, and 30% hydrogen peroxide were mixed in a mass ratio of 2.0:3.3:350, and stirred vigorously for 15 minutes.

Embodiment 320

[0039] Preparation of the ultrastable Y-type zeolite catalyst of embodiment 3.20% loading sodium tungstate

[0040] Accurately weigh 10g of sodium tungstate and dissolve it in 100ml of ethanol water solution (volume ratio of ethanol / water is 1 / 1), stir until dissolved, add 50g of ultra-stable Y-type zeolite with particle size above 200 mesh, and stir at room temperature for a long time Make the wetting balance, then evaporate the obtained suspension to dryness, dry it at room temperature, and then dry it at 120°C for 24 hours to obtain an ultrastable Y-type zeolite catalyst loaded with sodium tungstate.

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Abstract

The invention relates to a catalytic oxidation system and the application thereof in the synthesis of Tazobactam. The catalytic oxidation system formed a tungstate catalyst or a molybdate catalyst and a hydrogen peroxide oxidant is applied to the synthesis of Tazobactam to prepare a penicillanic acid sulfoxide intermediate I by catalytizing and oxidizing penicillanic acid. The reaction is characterized by high yield, good reaction selectivity, recyclable catalyst, and the like, required by green chemistry, wherein, R1 represents a carboxyl blocking group; R2 and R3 can be groups of the same pair or groups of different pair, such as H, halogen molecules, NH2, amide groups, and the like.

Description

technical field [0001] The invention relates to a catalytic oxidation system composed of peroxytungsten / molybdate catalyst and hydrogen peroxide, and the application of the system in the preparation of an important intermediate-penicillanic acid sulfoxide in the synthesis of tazobactam, which belongs to the field of chemical technology. Background technique [0002] The penicillanic acid sulfoxide compound I prepared from 6-aminopenicillanic acid (6-APA) is an important intermediate for the synthesis of a novel β-lactamase inhibitor-tazobactam. It is also a key intermediate necessary for ring expansion to obtain carbacephem and oxycephem cephalosporin nuclei. [0003] [0004] Wherein, R1 represents a carboxyl protecting group; R2 and R3 can be the same pair or different groups, such as H, halogen molecules, NH2, amide groups, etc. [0005] The quality of intermediate penicillanic acid sulfoxide I is directly related to the next step reaction of tazobactam synthesis and ...

Claims

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Application Information

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IPC IPC(8): C07D499/04C07D499/86
CPCY02P20/584
Inventor 梁新魁聂爱华刘金兰郝春波吴柯李保勇
Owner 山东安信制药有限公司
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