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Production method for synthesizing pregnenolone acetate from ticogenin

A technology of monoenolone acetate and sisal saponin, which is applied in the chemical industry, can solve problems such as incomplete reaction, low conversion rate and yield, and difficult centrifugation, so as to reduce production costs, improve production efficiency, and improve product quality. The effect of purity

Active Publication Date: 2013-05-22
湖北民生生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problems are as follows ①Sisal saponin has a structure of 1, 2-ring trans-fused 5a-H steroidal carbon price, and the ring-opening cracking reaction rate is different ②The purity of sisal saponin is low, with a content of 88-92 ﹪, Improper material ratio can easily lead to too many impurities after chemical reaction ③The extract after chemical reaction has a lot of oily substances, and the conventional washing is easy to emulsify, and the effect is poor
④ Centrifugation is difficult, each batch of material is centrifuged for 8-10 hours, and the mother liquor is not easy to handle
These circumstances lead to low product yield, low melting point of the finished product: 152-155°C, content: about 90% (HPLC external standard method), unqualified clarity, too much suspended matter after dissolution, and downstream products due to product quality problems Low conversion rate and yield, incomplete reaction

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1) Throw 100g of sisal saponin, add 80g of acetic acid and 140g of acetic anhydride, and heat to carry out the ring-opening cracking reaction. The temperature is 218°C, the pressure is 0.65MPa and the ring opening is completed; the material is added to the oxidative hydrolysis reaction bottle containing 250g of acetic acid, and the temperature of the material is 12°C through -10~-5°C brine, and the mass concentration is 38 % of chromic anhydride oxidizing agent is added in the oxidation hydrolysis reaction bottle to carry out the oxidation reaction. The temperature rises to 98°C and the reaction time is 45 minutes. First, the acetic acid is recovered by atmospheric distillation and then the acetic acid is recovered under reduced pressure to 350g. After the reaction is completed, the solution after the reaction is ready for use;

[0032] 2) Add the solution obtained in step 1) into an extraction bottle, add 800 mL of cyclohexane into the extraction bottle, stir for 25 min...

Embodiment 2

[0036] 1) Throw 10kg of sisal saponin, add 8kg of acetic acid and 15kg of acetic anhydride, heat to carry out the ring-opening cracking reaction, when the temperature rises to 208°C and the internal pressure reaches 0.48MPa, turn off the power and time the ring-opening for 65 minutes, and finally react The inner temperature of the kettle is 225°C, and the pressure is 0.65MPa, and the ring opening is completed; the material is pressed into the oxidation hydrolysis tank filled with 25L acetic acid, cooled to 12°C with chilled water, and the chromic anhydride oxidant with a mass concentration of 38.5% is quickly added to the oxidation tank , carry out the oxidation reaction, the temperature rises to 98°C and the reaction is timed for 45 minutes. First, the acetic acid is recovered by distillation under normal pressure, and then the acetic acid is recovered under reduced pressure to 35L. After the reaction is completed, the solution after the reaction is ready for use;

[0037] 2) ...

Embodiment 3

[0041] 1) Throw 160kg of sisal saponin, add 192kg of acetic acid, 256kg of acetic anhydride, and 60kg of mother liquor to carry out the ring-opening cracking reaction. When the temperature rises to 210°C and the internal pressure reaches 0.49MPa, turn off the power and count the ring-opening for 65 minutes. Finally, the internal temperature is 225°C and the pressure is 0.65MPa, and the ring opening is completed; the material is pressed into the oxidation hydrolysis tank equipped with 400kg of acetic acid, cooled to 12°C with chilled water, and the chromic anhydride oxidant with a mass concentration of 40% is quickly added to the oxidation tank. , carry out the oxidation reaction, the temperature rises to 98°C and the reaction is timed for 40 minutes, the acetic acid is firstly recovered by atmospheric pressure distillation, and then the acetic acid is recovered under reduced pressure to 550L. After the reaction is completed, the solution after the reaction is ready for use;

[...

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PUM

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Abstract

The invention relates to a production method for synthesizing pregnenolone acetate with ticogenin, which comprises the following steps: by using ticogenin as a raw material, acetic acid as a solvent and acetic anhydride as an acylating agent, carrying out pressurized ring-opening reaction, and carrying out oxydrolysis with chromic anhydride to obtain a compound reaction solution; extracting, washing with alkali, washing with water, filtering, concentrating under reduced pressure, crystallizing, and centrifuging to obtain a pregnenolone acetate crude product; and finally, recrystallizing to obtain the pregnenolone acetate. The method provided by the invention has the advantages of proper reaction conditions, high total yield, high product purity and low production cost, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical industry, and relates to a preparation method of a steroid hormone pharmaceutical compound, in particular a production method for synthesizing monoenolone acetate from sisal saponin. Background technique [0002] Monoenolone acetate, chemical name: 3β-hydroxypregn-5-en-20-one-3-acetate, molecular formula C 23 h 34 o 3 , the structural formula is: [0003] [0004] Monoenolone acetate is an important intermediate for the synthesis of androgenic anabolic hormones, family planning drugs, corticosteroids and other steroid drugs. [0005] The production process of using sisal saponin to produce monoene was reported abroad in the 1970s. The main production method is to learn from the reaction principle of diene process and has been used to this day. Domestic production of monoenolone acetate using sisal saponin started Later, the progress was slow, and the yield of monoenolone acetate produced from sisal...

Claims

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Application Information

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IPC IPC(8): C07J13/00
Inventor 陈少华裴胜汛
Owner 湖北民生生物医药有限公司
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