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Novel method for preparing substituted thenoic acid ester and uses thereof

A technology of thiophene formate and chloroacetic acid, applied in directions such as organic chemistry, can solve the problems of increased manufacturing cost, increased risk of environmental damage, and high cost of bromoacetate and phase transfer catalyst

Inactive Publication Date: 2008-03-12
BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although this patent has improved reaction efficiency by using phase-transfer catalyst, the cost of bromoacetate and phase-transfer catalyst that it uses is still higher, and bromoacetate is well known in the art to the strong stimulation of organisms, and this just Increased risk of damage to the environment and increased manufacturing costs

Method used

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  • Novel method for preparing substituted thenoic acid ester and uses thereof
  • Novel method for preparing substituted thenoic acid ester and uses thereof
  • Novel method for preparing substituted thenoic acid ester and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: 5-Amino-3-(2-ethoxy-2-oxoethyl)-4-cyano-2-thiophenecarboxylic acid ethyl ester

[0027] 700 milliliters of ethanol, 500 grams of diethyl 3-oxoglutarate and 200 grams of malononitrile were respectively added into the reaction flask, stirred vigorously, 250 grams of morpholine were added, and stirred for 1 hour. Add 100 grams of sulfur powder and heat to reflux. The reaction was kept at reflux for 3 hours, cooled to room temperature, poured into 1500 ml of water, and a large amount of solids were precipitated. Filter, wash with 200 ml of water, and air-dry at 50°C until constant weight to obtain 520 g of light yellow solid, yield: 75%.

Embodiment 2

[0028] Example 2: 5-[Bis(2-ethoxy-2-oxoethyl)amino-3-(2-ethoxy-2-oxoethyl)-4-cyano-2-thiophenecarboxylic acid ethyl ester

[0029] Add 500 grams of ethyl 5-amino-3-(2-ethoxy-2-oxoethyl)-4-cyano-2-thiophenecarboxylate prepared according to Example 1 to 3000 ml of acetone, add 20 grams of trimethylbenzyl ammonium chloride, 600 grams of ethyl chloroacetate, and 500 grams of anhydrous potassium carbonate were stirred and heated to reflux. Keep the reflux reaction for 12 hours, cool to room temperature, filter, and concentrate the filtrate to dryness. Add 1000 ml of methanol, heat to reflux for 1 hour, stir in an ice-water bath for 5 hours, filter, and blow dry at 50° C. to constant weight to obtain 640 grams of white solid, yield: 80%.

Embodiment 3

[0030] Example 3: Strontium ranelate

[0031] 5-[bis(2-ethoxy-2-oxoethyl)amino-3-(2-ethoxy-2-oxoethyl)-4-cyano-2 prepared according to Example 2 - Add 300 grams of ethyl thiophenecarboxylate to 3000 milliliters of water, add 350 grams of strontium hydroxide, stir, and heat to reflux. Keep the reflux reaction for 6 hours, filter, and rinse with 300 ml of hot water. Vacuum-dried at 80°C to constant weight to obtain 315 g of white solid, yield: 93%.

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Abstract

The present invention relates to a preparation method of the substituted thiophene formate as shown in formula (I), wherein the R1, R2, R3 and R4 can be the same and can be different; and the R1, R2, R3 and R4 respectively represent the alkyl of the straight chain or branched-chain of C1-C10, or the aryl of C6-C12, wherein the aryl can be replaced with 1 to 4 substituted bases. The present invention provides a novel method of preparing the substituted thiophene formate as shown in formula (I); the method is more economical and less harmful to the environment. The compound of the formula (I) produced in the present invention can be used for the synthesis of strontium ranelate.

Description

field of invention [0001] The present invention relates to a new preparation method of substituted thiophene carboxylate represented by formula (I), [0002] [0003] The compound of formula (I) obtained according to the method of the present invention can be used to synthesize ranelic acid or ranelate and hydrates thereof. Background of the invention [0004] European patent EP0415850 discloses ranelic acid salts, preparation methods and therapeutic uses thereof, especially its strontium salt (strontium ranelate) has high pharmacological value, especially outstanding anti-osteoporosis properties. [0005] At present, anti-osteoporosis drugs are mainly bisphosphonates, including sodium alendronate, sodium ritidronate, etc. These bisphosphonates are cheap to manufacture. The medicinal specification of strontium ranelate is 2 grams / time, so reducing the cost of strontium ranelate is of great significance. [0006] Chinese patent CN1500783A discloses the synthetic method a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/38
Inventor 高雪松李勇
Owner BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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