A kind of preparation method of α-abortion-3,5-cracking-androst-5-one-3,17-dioic acid

An androstane and diacid technology is applied in the preparation field of carbocyclic compounds, can solve the problems of high price of iodate, lost products, large solvent consumption and the like, and achieves easy industrial implementation, mild reaction conditions and high raw material recovery rate. Effect

Active Publication Date: 2016-04-27
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the temperature of rejection filtration before acidification is higher, so that the precipitation of iodate is reduced, and the recovery rate is reduced. At the same time, because the price of iodate is relatively expensive, the water temperature of washing is too high to lose iodine salt, and the water temperature of washing is too low. Then the sodium salt of entrained A-abortion-3,5-cracking-androst-5-one-3,17-dioic acid in the iodate filter cake will increase, and the product will be lost
[0008] Therefore, the traditional production method consumes a lot of solvent, the recovery rate of iodate is low, the quality is poor, the yield is low, the cost is high, and the pollution of "three wastes" is large

Method used

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  • A kind of preparation method of α-abortion-3,5-cracking-androst-5-one-3,17-dioic acid
  • A kind of preparation method of α-abortion-3,5-cracking-androst-5-one-3,17-dioic acid
  • A kind of preparation method of α-abortion-3,5-cracking-androst-5-one-3,17-dioic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of A-carbo-3,5-cleavage-androst-5-one-3,17-dioic acid

[0034] At room temperature, in a 3000L enamel reaction kettle equipped with a thermometer, jacket and stirrer, add 1000L of water, stir, add 42kg of sodium carbonate, after dissolving, it becomes alkaline water, add 3-carbonyl-4-androstene-17β - 100kg of carboxylic acid, stirred and dissolved, cooled with circulating water in the jacket.

[0035] Oxidant preparation solution: In a 2000L enamel high-position dripping kettle equipped with a thermometer and a stirrer, add 1500L of water, stir, add 350kg of sodium periodate and 3kg of potassium permanganate, heat to 75-80°C and keep warm to dissolve.

[0036] When the temperature of the circulating water in the reaction kettle is lowered, slowly add the aqueous solution of the oxidant into the reaction kettle dropwise. After the addition is completed within 2 hours, the temperature is controlled at 25°C to 30°C, and the reaction is kept for 2 hou...

Embodiment 2

[0038] Example 2: Preparation of A-carbo-3,5-cleavage-androst-5-one-3,17-dioic acid

[0039] At room temperature, in a 3000L enamel reaction kettle equipped with a thermometer, jacket and stirrer, add 1000L of water, stir, add 53kg of sodium bicarbonate, and dissolve it to obtain alkaline water, add 3-carbonyl-4-androstene- 100kg of 17β-carboxylic acid was stirred and dissolved, and the jacket was cooled by circulating water.

[0040] Oxidant preparation solution: In a 2000L enamel high-position dripping kettle equipped with a thermometer and a stirrer, add 1500L of water, stir, add 350kg of sodium periodate and 3kg of potassium permanganate, heat to 75-80°C and keep warm to dissolve.

[0041] When the temperature of the circulating water in the reaction kettle is lowered, slowly drop the oxidizing agent solution into the reaction kettle. After 1.8 hours of dropping, keep the reaction at 25°C to 30°C for 2 hours, place the plate until the reaction is complete, and then cool do...

Embodiment 3

[0042] Example 3: Preparation of A-carbo-3,5-cleavage-androst-5-one-3,17-dioic acid

[0043] At room temperature, in a 3000L enamel reaction kettle equipped with a thermometer, jacket and stirrer, add 1000L of water, stir, add 16kg of sodium hydroxide, after it dissolves, it becomes alkaline water, add 3-carbonyl-4-androstene- 100kg of 17β-carboxylic acid was stirred and dissolved, and the jacket was cooled by circulating water.

[0044] Oxidant preparation solution: In a 2000L enamel high-position dripping kettle equipped with a thermometer and a stirrer, add 1500L of water, stir, add 350kg of sodium periodate and 3kg of potassium permanganate, heat to 75-80°C and keep warm to dissolve.

[0045] When the temperature of the circulating water in the reaction kettle is lowered, slowly drop the oxidant solution into the reaction kettle. After 1.8 hours of dropwise addition, keep the reaction at 25°C to 30°C for 2 hours, touch the plate until the reaction is complete, cool down to...

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Abstract

The invention provides a preparation method of A-nor-3, 5-cracking-androstane-5 -keto-3, 17-diacid. The preparation method comprises the following steps: (1), 3-carbonyl-4-androstene-17beta carboxylic acid is dissolved in alkaline water, and the temperature of the solution is controlled to be 20-40 DEG C; (2), an oxidizing agent which is an aqueous solution including sodium periodate and potassium permanganate is added, and reaction is performed continuously for 1-3 h after addition; (3), after sufficient reaction, cooling is performed by ice brine until the temperature is 0-5 DGE C, spin-filtering is performed, and a filter cake is washed by ice alkaline water at the temperature of 0-5 DEG C and spin-dried; and (4), a filtrate obtained from spin-filtering is acidized and spin-filtered, and a filter cake is washed until an eluate is neutral. According to the provided method, an organic solvent is not used, accordingly, the method is economic and environment-friendly, and aftertreatment is simple; reaction is performed under homogeneous phase condition, the reaction temperature and iodate separation temperature are lower, the product quality is good, the yield is high, the iodate recovery rate is high, and the cost is low. Therefore, a product with higher purity can be obtained at high yield and low cost with the method.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a preparation method of carbocyclic compounds. Background technique [0002] The pharmaceutical intermediates for the preparation of dutasteride (dutasteride, 1) include A-abortion-3,5-cleavage-androst-5-one-3,17-dioic acid, which can be obtained from commercially available 3-carbonyl-4- Androstene-17β carboxylic acid comes from oxidative ring opening, and its general reaction formula is as follows: [0003] [0004] The current traditional production method introduced in the literature is: with 3-carbonyl-4-androstene-17β carboxylic acid methyl ester or 3-carbonyl-4-androstene-17β carboxylic acid amide as substrate, with tert-butanol, water Mixed solvent, sodium carbonate as alkali catalysis, sodium periodate and potassium permanganate aqueous solution oxidation (US20060046994A1; CN101863956A). Traditional production methods have the following defects: [0005]...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C62/24C07C51/31
Inventor 唐小海左前进甘红星谢来宾
Owner HUNAN KEREY BIOTECH
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