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Synthesis method of triene acetate compound

A technology of triene acetate and synthesis method, applied in the direction of steroids, organic chemistry, etc., can solve the problem that the yield is only 60%, and achieve the effect of inhibiting the formation of rearrangement impurities

Inactive Publication Date: 2020-01-21
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

resulting in a yield of only 60%

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  • Synthesis method of triene acetate compound
  • Synthesis method of triene acetate compound

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Embodiment 1

[0018] Add 588g of pyridine into a clean and dry reaction flask, under the protection of nitrogen, start stirring, add 55g of N-chlorosuccinimide and 200g of 4-dimethylaminopyridine, and then cool the system down to -30~-15°C . Control the temperature at -30--15°C, and add the prepared sulfur dioxide pyridine solution (98g of pyridine and 34g of sulfur dioxide gas) dropwise into the reaction system for about half an hour. After the dropwise addition was completed, the temperature was controlled at -30 to -20°C, and 100 g of anecortax acetate was added five times with an interval of 20 to 30 minutes each time. After the addition was completed, the bottle wall was rinsed with a small amount of pyridine. Insulate at -30~-15℃ and react for 60~80 minutes. After the incubation was completed, TLC detection was performed to ensure that the reaction was complete. If the reaction is not complete, extend the reaction time until it is qualified. Add 2000g of water and 1080g of concentr...

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Abstract

The invention belongs to the technical field of steroid hormone preparation, in particular to a synthesis method of a triene acetate compound. The preparation method comprises the following steps: under the participation of 4-dimethylaminopyridine, removing 17-site hydroxyl of the anecortave acetate by using an N-chlorosuccinimide and a sulfur dioxide pyridine solution; and after the reaction is finished, performing crystallization to obtain the triene acetate compound. The 4-dimethylaminopyridine is added into the reaction system, an intermediate is stabilized, generation of rearrangement impurities is well inhibited, and the content of the rearrangement impurities in the system is reduced from 12% to 2%, so that the triene acetate compound is obtained at a high yield, with the purity reaching 99%, and the yield being 80% or above.

Description

technical field [0001] The invention belongs to the technical field of preparation of steroid hormones, and in particular relates to a synthesis method of triene acetate. Background technique [0002] Triene acetate (CAS: 23460-76-6) is the starting material for the synthesis of steroid hormone drug halcinonide. The currently reported method is the preparation method of CN201510793590-△16 steroids, which describes the use of anecorta acetate, oxidant and sulfur dioxide to react in an organic solvent to generate acetate triene, with a weight yield of 94% and a purity of 98%. US3210341 reported the use of pyridine as a solvent and N-bromosuccinimide or N-chlorosuccinimide to remove the 17-position hydroxyl group. Trying the operation method of US3210341, it is found that there is a 12% impurity, as shown in the following formula, which is confirmed by the structure as an 18-position methyl rearrangement impurity. Resulting in a yield of only 60%. [0003] [0004] When ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
CPCC07J5/0015
Inventor 靳志忠刘喜荣曾春玲孙晓明
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD