Preparation method of terbutaline sulfate

A technology of terbutaline sulfate and concentrated sulfuric acid, which is applied in the field of medicine and chemical industry, can solve the problems of increased post-processing cost and environmental protection pressure of mixed solvents, high market price of raw materials, cumbersome post-processing, etc., to avoid high energy consumption operating conditions The effect of using, avoiding the introduction of water and inorganic salts, and reducing the difficulty of post-reaction treatment

Active Publication Date: 2017-12-26
SHIJIAZHUANG NO 4 PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology provides various benefits such as improved yields or better quality control over certain chemical reactions involving specific compounds like tertiary amines (TAs). These improvements include reducing unwanted side products formed during these processes while maintaining desired results through more efficient production methods with less waste materials generated compared to traditional ways. Additionally, this new approach simplifies the manufacturing process without requiring expensive equipment and involves no harmful substances being released into the atmosphere when treated properly. Overall, this innovative solution improves overall performance and cost savings associated therewith

Problems solved by technology

Technical Problem addressed in this patents relates to improving the efficiency and accuracy of producing stable and pure beta -block copolyetheresterase-4 enzyme(BACE)-binding agent or analogues thereof called betataladienesulphoxane (BBTS). However, current methods have limitations including difficulty controlling reaction rates due to different reactants' chemical structures, excessive amounts of organics during processing, complicated procedures involving multiple steps, increased cost per treatment compared to existing techniques like ion exchange resins, etc., and reduced yields caused by incomplete conversion between certain groups.

Method used

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  • Preparation method of terbutaline sulfate
  • Preparation method of terbutaline sulfate
  • Preparation method of terbutaline sulfate

Examples

Experimental program
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Embodiment 1

[0042]Add 1.18kg of the compound of formula I to 13.8L of glacial acetic acid and 59g of palladium carbon, replace with nitrogen 6 times, hydrogen 6 times, and stir at 60°C under normal pressure for 5 hours in the dark. Cool down to 10-15°C, suction filter under nitrogen atmosphere, place the suction filtrate in a reaction flask, add acetic acid solution of concentrated sulfuric acid equivalent to 0.5eq of the compound of formula I (mass volume concentration is 5%) under nitrogen protection, stir for 15min, Transfer to a distillation flask, replace with nitrogen, distill under reduced pressure, concentrate, cool down to room temperature, add 650ml of methanol, stir and crystallize under nitrogen atmosphere for 30min, drop to 10-15℃ for 1.5h, suction filter to obtain a white crystalline solid 645g, yield 98.4%, purity 99.87%.

Embodiment 2

[0044] Add 1.19 kg of the compound of formula II to 17.8 L of glacial acetic acid and 119 g of Ni, replace with nitrogen 6 times and hydrogen 6 times, and stir at 50°C under normal pressure for 4 hours in the dark. Cool down to 10-15°C, suction filter under a nitrogen atmosphere, place the suction filtrate in a reaction flask, add an acetic acid solution of concentrated sulfuric acid equivalent to 0.505 eq of the compound of formula I (mass volume concentration: 8%) under nitrogen protection, and stir for 20 minutes. Transfer to a distillation flask, replace with nitrogen, distill under reduced pressure, concentrate, cool down to room temperature, add methanol, stir and crystallize under a nitrogen atmosphere for 30 minutes, drop to 10-15°C for 2 hours, and filter with suction to obtain 652 g of a white crystalline solid. Yield 99.1%, purity 99.83%.

Embodiment 3

[0046] Add 1.18kg formula I compound to 11.8L glacial acetic acid and 59g Pd(OH) 2 , 6 times of nitrogen replacement, 6 times of hydrogen replacement, stirring at 40° C. under normal pressure in the dark for 5 h. Cool down to 10-15°C, suction filter under nitrogen atmosphere, place the suction filtrate in a reaction flask, add acetic acid solution of concentrated sulfuric acid equivalent to 0.495eq of the compound of formula I (mass volume concentration is 5%) under nitrogen protection, and stir for 15min. Transfer to a distillation flask, replace with nitrogen, distill under reduced pressure, concentrate, cool down to room temperature, add 1300ml of methanol, stir and crystallize under nitrogen atmosphere for 30min, drop to 10-15°C for 1.5h, and suction filter to obtain a white crystalline solid 642g, yield 98.0%, purity 99.0%.

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Abstract

The invention relates to a preparation method of terbutaline sulfate, which comprises the following steps: dissolving a compound of formula I or formula II into a solvent A, adding a metal catalyst for catalytic hydrogenation, so as to obtain 5-[2-[(1,1-dimethylethyl)amido]-1-ethoxyl]-1,3-resorcinol; after the reaction is finished, filtering, collecting filter liquor, adding a certain amount of concentrated sulfuric acid in the filter liquor, after stirring is stopped, recycling the solvent A, adding a solvent B into a residue, stirring to separate out a white crystal substance, performing suction filtration, thus obtaining the terbutaline sulfate. According to the method provided by the invention, the treating difficulty after the reaction is greatly reduced, the introduction of water and inorganic salt is avoided, and the product content is high; furthermore, the stability of the terbutaline sulfate is obviously improved by distilling the product under acidic conditions, the catalyst and the reaction solvents are recyclable, so that the environmental protection pressure is greatly reduced.

Description

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Claims

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Application Information

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Owner SHIJIAZHUANG NO 4 PHARMA
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