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Synthesis method of dexamethasone palmitate

A technology of dexamethasone palmitate and a synthesis method, applied in the directions of steroids, organic chemistry, etc., can solve the problems of complicated separation steps of catalysts and products, unreusable catalysts, discharge pollution of corrosive waste water, etc. The separation, post-treatment and purification of the reaction system are convenient, and the effect of not corroding equipment

Active Publication Date: 2019-07-23
JIANGSU YUANDA XIANLE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Catalysts can be divided into homogeneous catalysts and heterogeneous catalysts. Homogeneous catalysts are soluble in the reaction system. Single-phase catalysis is performed during the reaction process, and the catalysis is relatively sufficient. However, there are many shortcomings in production and application: the catalyst cannot be reused, recycled Difficult, the separation steps of catalyst and product are cumbersome, corrosive and pollution caused by waste water discharge, etc.

Method used

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  • Synthesis method of dexamethasone palmitate
  • Synthesis method of dexamethasone palmitate
  • Synthesis method of dexamethasone palmitate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Under the protection of nitrogen, add 540g (2.0mol) of methyl palmitate to a 1000mL three-necked flask, raise the temperature to about 40°C, add 60g (0.153mol) of dexamethasone, 12g of cesium oxide supported on γ-alumina, and 3g of polyethylene glycol Glycol 400, adjust the vacuum degree to 0.07MPa, heat up to 80°C, react for 3h, TLC monitors the completion of the raw material reaction (developing solvent, petroleum ether: ethyl acetate = 1:1), filter while hot, wash the filter with 90g of acetone Cake, the filtrate was cooled to 0°C, crystallized, and 88.7 g of the product was obtained by filtration, with a yield of 92% and a purity of 99.60%. The filter cake is dried and recycled, and the mother liquor after crystallization and filtration is evaporated to remove acetone to obtain a mixture of methyl palmitate and the product, which is recycled.

Embodiment 2

[0038] Under nitrogen protection, add 540g (2.0mol) of methyl palmitate into a 1000mL three-necked flask, raise the temperature to about 40°C, add 60g (0.153mol) of dexamethasone, 3g of calcium oxide loaded on molecular sieves, 0.6g of polyethylene glycol Alcohol 600, adjust the vacuum to 0.05MPa, heat up to 50°C, react for 10h, TLC monitors the completion of the reaction of raw materials (developing solvent, petroleum ether: ethyl acetate = 1:1), filter while hot, and wash the filter cake with 225g methanol , the filtrate was cooled to -10°C, crystallized, and 87g of the product was obtained by filtration, with a yield of 90.25% and a purity of 99.30%. The filter cake is dried and reused mechanically, the mother liquor after crystallization and filtration, and the mixture of methyl palmitate and the product obtained after distilling off methanol is recycled mechanically.

Embodiment 3

[0040] Under nitrogen protection, add 540g (2.0mol) of methyl palmitate into a 1000mL three-necked flask, raise the temperature to about 40°C, add 60g (0.153mol) of dexamethasone, 6g of potassium oxide loaded on molecular sieves, 1.8g of polyethylene glycol Alcohol 800, adjust the vacuum degree to 0.1MPa, raise the temperature to 70°C, react for 6h, monitor the completion of the raw material reaction by TLC (developing solvent, petroleum ether: ethyl acetate = 1:1), filter while hot, and wash the filter cake with 300g ethanol , the filtrate was cooled to 10°C, crystallized, and 85.8 g of the product was obtained by filtration, with a yield of 89% and a purity of 99.80%. The filter cake is dried and reused mechanically. The mother liquor after crystallization and filtration is evaporated to remove ethanol and the mixture of methyl palmitate and the product is recycled.

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Abstract

The invention relates to a synthesis method of dexamethasone palmitate. The method comprises the steps as follows: dexamethasone and methyl palmitate are subjected to transesterification under catalysis of solid alkali and a phase transfer catalyst to obtain a target product; a mixture of methyl palmitate and the product obtained after a solvent is removed from solid alkali and the phase transfercatalyst by evaporation is recycled. The method is mild in reaction condition, green, environmentally friendly, simple, efficient and energy-saving, raw materials are easy to obtain, the production cost is reduced, the operation environment is improved, and the method is convenient to operate, high in automation degree and particularly prone to industrialization.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing dexamethasone palmitate. Background technique [0002] The chemical name of Dexamethasone palmitate is 9-fluoro-11β, 17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione-21-palmitic acid Ester is a non-specific steroidal anti-inflammatory drug, which is mainly used clinically for the treatment of chronic rheumatoid arthritis, asthma, systemic infection and various malignant lymphomas. Dexamethasone palmitate itself has no activity. The 21-hydroxyl of the active ingredient dexamethasone is esterified to generate dexamethasone palmitate, which greatly enhances the fat solubility of the drug. After administration, it tends to inflammatory tissue It is easy to concentrate in the inflammatory site. Under the action of esterification enzyme, it is hydrolyzed and deesterified to form its biological metabolite dexamethasone, which plays a targeting...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
CPCC07J5/0076
Inventor 刘年金胡丽娟张邦国赵百合杜艳
Owner JIANGSU YUANDA XIANLE PHARMA
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