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Synthesizing method of sulbactam acid

A synthesis method and technology of sulbactam acid, applied in the field of synthesis of sulbactam acid, can solve the problems of high cost, low yield, pollute the environment and the like, and achieve the effects of low cost and high yield

Active Publication Date: 2015-04-08
LIANYUNGANG HENGFEI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to overcome the defects of low yield, high cost and environmental pollution in the existing sulbactamic acid synthesis method, and provide a new sulbactam acid synthesis method

Method used

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  • Synthesizing method of sulbactam acid
  • Synthesizing method of sulbactam acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1. Add 1000kg of ethyl acetate into a 1500L reaction pot, then stir and cool to 0°C, inhale 150kg of bromine, add sulfuric acid solution dropwise (take 43.2kg of sulfuric acid + 200kg of water), control the temperature not to exceed 5°C, cool to 4°C, Add 57.6kg of sodium nitrite in several times, control the temperature not to exceed 5°C, keep warm for 20 minutes, then slowly add 90kg of 6-APA at 4°C, and react at 10°C for 0.5 hours after the addition is complete. Add dropwise 10% sodium bisulfite aqueous solution until the bromine color disappears, and the reaction solution is light yellow. Stop stirring when no yellow gas escapes, let stand to separate layers, and extract the lower aqueous layer twice with ethyl acetate (400kg×2 ), the water layer after the extraction was recovered bromine, the ethyl acetate layer was combined to the neutralization pot and stirred and cooled, the pH was adjusted to 7 with sodium hydroxide solution, the layers were static, and the ethyl...

Embodiment 2

[0028] 1. Add 1000kg of ethyl acetate into a 1500L reaction pot, then stir and cool to 0°C, inhale 150kg of bromine, add sulfuric acid solution dropwise (take 43.2kg of sulfuric acid + 200kg of water), control the temperature not to exceed 5°C, cool to 4°C, Add 57.6kg of sodium nitrite in several times, control the temperature not to exceed 5°C, keep warm for 30 minutes, then slowly add 90kg of 6-APA at 8°C, and react at 10°C for 40 minutes after the addition is complete. Add dropwise 10% sodium bisulfite aqueous solution until the bromine color disappears, and the reaction solution is light yellow. Stop stirring when no yellow gas escapes, let stand to separate layers, and extract the lower aqueous layer twice with ethyl acetate (400kg×2 ), the water layer after the extraction is recovered bromine, the ethyl acetate layer is combined to the neutralization pot and stirred and cooled, the pH is adjusted to 7 with sodium hydroxide solution, the layers are static, the ethyl acetat...

Embodiment 3

[0033] 1. Add 1000kg of ethyl acetate into a 1500L reaction pot, then stir and cool to 0°C, inhale 150kg of bromine, add sulfuric acid solution dropwise (take 43.2kg of sulfuric acid + 200kg of water), control the temperature not to exceed 5°C, cool to 4°C, Add 57.6kg of sodium nitrite in several times, control the temperature not to exceed 5°C, keep warm for 30 minutes, then slowly add 90kg of 6-APA at 10°C, and react at 10°C for 0.4 hours after the addition is completed. Add dropwise 10% sodium bisulfite aqueous solution until the bromine color disappears, and the reaction solution is light yellow. Stop stirring when no yellow gas escapes, let stand to separate layers, and extract the lower aqueous layer twice with ethyl acetate (400kg×2 ), the water layer after the extraction is recovered bromine, the ethyl acetate layer is combined to the neutralization pot and stirred and cooled, the pH is adjusted to 7 with sodium hydroxide solution, the layers are static, the ethyl aceta...

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Abstract

The invention discloses a synthesizing method of sulbactam acid. The method comprises the steps that: (1) under the existence of a strong acid, 6-aminopenicillanic acid, a diazotization reagent, and bromine or bromide are subjected to an insulation reaction in an organic solvent; excessive bromine is reduced; and a reaction product is extracted to a water layer; (2) an oxidant is dropped into the water-layer reaction product, and an insulation reaction is carried out; when the reaction is finished, a pH value is regulated; excessive potassium permanganate is reduced; an organic solvent is added, such that a reaction product is extracted to an organic solvent layer; (3) a catalyst is added into the organic-solvent layer product, such that hydrogenation bromine-removing is carried out; a reaction product is extracted to an organic-solvent layer; and distillation and crystallization are carried out. The organic solvent is ethyl acetate. According to the invention, ethyl acetate is adopted as the organic solvent in a four-step reaction, such that solvent consumption of the whole reaction is greatly reduced, and product total yield is effectively improved. With the method provided by the invention, by-product in the reaction can be comprehensively utilized, and advantages such as high yield, low cost, clean production, and the like are provided.

Description

technical field [0001] The invention relates to a method for synthesizing a beta-lactamase inhibitor, in particular to a method for synthesizing sulbactamic acid, which belongs to the field of sulbactamic acid synthesis. Background technique [0002] The chemical name of sulbactamic acid: 4-thio-1-heterobicyclo[β,2,0]heptane-2-carboxylic acid-dimethyl-7-oxo-4.4-dioxide; its structural formula is as follows: [0003] [0004] Physical and chemical properties of sulbactam acid: This product is off-white or light yellow crystalline powder, easily soluble in water, alcohol, ester and hardly soluble in ether; drug use: Sulbactam sodium is a diuretic antibacterial drug and penicillin Enzyme inhibitor of choice for antimicrobials. It belongs to atypical β-lactam drugs. Due to the long-term and large-scale use of cephalosporins and penicillins, β-lactamase has produced antibiotic resistance, and sulbactam and cephalosporins and penicillins After compatible use, the problem of a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/86C07D499/04
Inventor 张桂友丁海风王玉霞
Owner LIANYUNGANG HENGFEI PHARMA
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