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Preparation method for intermediate (5E, 9E)-farnesyl acetone of teprenone

A technology of acacia acetone and teprenone, which is applied in the field of chemical synthesis of chemicals and intermediates, can solve the problems of low product purity, difficulty in large-scale production and the like, and achieves high purity, easy pollution treatment, and yield. high effect

Inactive Publication Date: 2015-03-25
岳阳新华达制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the small difference in the boiling points of the two cis-trans isomers, the purity of the obtained product is not high, and it is actually difficult to produce on a large scale.

Method used

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  • Preparation method for intermediate (5E, 9E)-farnesyl acetone of teprenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1. Synthesis of (2E,6E)-farnesyl chloride

[0043]

[0044] Add 21.51g of triethylamine to 43.14g of (2E,6E)-farnesol, then add 8.23g of lithium chloride dissolved in 100ml of DMF, cool down to 0°C, add dropwise 16.56ml of methanesulfonyl chloride, 10 The dropwise addition was completed in 1 minute, and the temperature was controlled at 0°C for 2 hours. No raw materials remained. Wash with 5% aqueous sodium bicarbonate solution and 5% normal saline, dehydrate with anhydrous magnesium sulfate, and desolventize the filtrate under reduced pressure to obtain 44.81 g of light yellow oily liquid.

[0045] 2. Synthesis of (5E,9E)-Ethoxycarboethyl Albizia Acetone

[0046]

[0047] Add 24.5g of sodium ethylate to 98ml of absolute ethanol, cool down to 0°C, add 46.85g of ethyl acetoacetate dropwise, maintain the temperature for 20 minutes, add dropwise 55ml of 43.29g of (2E, 6E )-Farnesyl chloride in dioxane solution, after the dropwise addition, naturally rise to r...

Embodiment 2

[0052] 1. Synthesis of (2E,6E)-farnesyl chloride

[0053]

[0054] Add 21.51g of triethylamine to 43.14g of (2E,6E)-farnesol, then add 8.23g of lithium chloride dissolved in 100ml of DMF, cool down to -10°C, add dropwise 16.56ml of methanesulfonyl chloride, The dropwise addition was completed in 10 minutes, and the temperature was controlled at 0°C for 2 hours. No raw materials remained. Pour the reaction liquid into 500ml ice water, extract with 3×100ml n-hexane, combine the organic phases, and use 5% potassium bisulfate aqueous solution and purified water respectively. , 5% aqueous sodium bicarbonate solution, 5% normal saline washing, dehydration with anhydrous magnesium sulfate, and desolvation of the filtrate under reduced pressure to obtain 44.01 g of light yellow oily liquid.

[0055] 2. Synthesis of (5E,9E)-Ethoxycarboethyl Albizia Acetone

[0056]

[0057] Add 24.5g of sodium ethylate to 98ml of absolute ethanol, cool down to 0°C, add 46.85g of ethyl ac...

Embodiment 3

[0062] 1. Synthesis of (2E,6E)-farnesyl chloride

[0063]

[0064] Add 21.51g of triethylamine to 43.14g of (2E,6E)-farnesol, then add 8.23g of lithium chloride dissolved in 100ml of DMF, cool down to 0°C, add dropwise 16.56ml of methanesulfonyl chloride, 10 The dropwise addition was completed in 1 minute, and the temperature was controlled at 0°C for 2 hours. No raw materials remained. Wash with 5% aqueous sodium bicarbonate solution and 5% normal saline, dehydrate with anhydrous magnesium sulfate, and desolventize the filtrate under reduced pressure to obtain 44.55 g of light yellow oily liquid.

[0065] 2. Synthesis of (5E,9E)-Ethoxycarboethyl Albizia Acetone

[0066]

[0067] Add 24.5g of sodium ethylate to 98ml of absolute ethanol, cool down to 0°C, add 46.85g of ethyl acetoacetate dropwise, maintain the temperature for 20 minutes, add dropwise 55ml of 43.29g of (2E, 6E )-Farnesyl chloride in dioxane solution, after the dropwise addition, naturally rise to...

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Abstract

The invention discloses a preparation method for an intermediate (5E, 9E)-farnesyl acetone of teprenone. The preparation method comprises the following steps: (1) carrying out reaction on (2E, 6E)-farnesol together with methanesulfonyl chloride and lithium chloride to obtain (2E, 6E)-farnesyl chloride; (2) carrying out reaction (2E, 6E)-farnesyl chloride together with ethyl acetoacetate and sodium ethoxide to generate (5E, 9E)-ethoxycarbonyl ethyl farnesyl acetone; and (3) decarboxylating (5E, 9E)-ethoxycarbonyl ethyl farnesyl acetone in the alkaline solution of potassium hydroxide by saponifying to obtain the (5E, 9E)-farnesyl acetone. The innovative synthesis process is used for preparing the (5E, 9E)-farnesyl acetone, the toxicity of adopted raw materials and by-products are low, and the raw materials and the by-products are easy to treat. In addition, materials react under mild reaction conditions, the preparation method is easy to operate, the yield and the purity of the (5E, 9E)-farnesyl acetone are high, and the content of isomers in (5E, 9E)-farnesyl acetone is low.

Description

technical field [0001] The invention relates to a preparation method of acacia acetone, an intermediate (5E, 9E) of the drug teprenone. The invention belongs to the technical field of chemical synthesis of chemicals and intermediates. Background technique [0002] Teprenone, also known as diniurongeranyl acetone, is a terpene-based gastric mucosal protective agent with broad-spectrum anti-ulcer effects, and has strong anti-ulcer effects and Improvement of gastric mucosal lesions. It is clinically used to treat gastric ulcer and chronic gastritis caused by various reasons, gastric mucosal injury induced by non-steroidal anti-inflammatory drugs, and combined use with antacids to treat peptic ulcer; prevent and improve gastric mucosal injury caused by HP infection , prevention of NSAIDs-related gastroenteropathy, prevention and improvement of gastric mucosal damage in portal hypertensive gastropathy, combined with antacids in the treatment of peptic ulcer, etc. Teprenone, as...

Claims

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Application Information

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IPC IPC(8): C07C49/203C07C45/65
CPCC07C17/16C07C45/65C07C67/343C07C21/215C07C69/738C07C49/203
Inventor 杨勇郭凌云随裕敏
Owner 岳阳新华达制药有限公司
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