Compound and method for synthesizing 8-hydroxy-2,2,14,14-tetramethyl pentadecanedioic acid by adopting compound

A technology of tetramethylpentadecane and compounds, which is applied in the field of chemical synthesis, can solve problems such as difficulty in guaranteeing product quality and impracticability, and achieve the effect of short steps and mild conditions

Active Publication Date: 2020-05-19
AURISCO PHARM(TIANJIN) INC +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires all the organic solvents to be evaporated to dryness to obtain the product, which cannot be realized in industrial production, and the product obtained by this method has not undergone any crystallization or recrystallization, and the product quality is difficult to guarantee

Method used

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  • Compound and method for synthesizing 8-hydroxy-2,2,14,14-tetramethyl pentadecanedioic acid by adopting compound
  • Compound and method for synthesizing 8-hydroxy-2,2,14,14-tetramethyl pentadecanedioic acid by adopting compound
  • Compound and method for synthesizing 8-hydroxy-2,2,14,14-tetramethyl pentadecanedioic acid by adopting compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Add 300g (2.58mol) of ethyl isobutyrate and 724.9g (3.36mol, 1.3eq) of 1,4-dibromobutane into 1500ml of tetrahydrofuran, start stirring, cool down to -10~0℃, and control the temperature to -10~ Add 1.36L lithium diisopropylamide (2N, 2.71mol, 1.05eq.) dropwise at 10°C. After dropping, GC shows that the conversion rate is 76.14%. Add 100ml of water to quench the reaction, and use 3N HCl to adjust the pH to 6-7 (980ml ), liquid separation, the organic phase was washed with 600ml*2 saturated sodium chloride, concentrated, rectified, and vacuum degree of 180Pa was collected, and the fraction at 82-87°C was obtained to obtain 423.7g of 2,2-dimethyl-6-bromohexanoic acid Ethyl ester, yield: 65.3%.

[0072] Other examples are described below, and the differences from Embodiment 1 are shown in the table below:

[0073]

[0074]

[0075] Second and third steps

[0076]

Embodiment 24

[0078] Add 60g (239mmol) ethyl 2,2-dimethyl-6-bromohexanoate to 300ml ethanol, and add 26.6g (131mmol) diethyl 1,3-acetonedicarboxylate, 49.5g (359mmol ) Potassium carbonate, 39.7g (239mmol) potassium iodide, heat up to 65-70°C, keep warm for 20 hours, cool the system to room temperature, filter, rinse the filter cake with 50ml ethanol, add 300ml purified water to the mother liquor, add 43g (1075mmol) Sodium hydroxide, heated to reflux, kept reflux for 4 hours, after NMR traced the reaction, concentrated the system to dryness, added 400ml water to dissolve, extracted with 200ml methyl tert-butyl ether after dissolution, after liquid separation, used 36% concentrated hydrochloric acid Adjust the pH of the water phase to 1-2, control the temperature of the system at 0-10°C, stir for 15 minutes, filter, dissolve the filter cake with 300ml of methyl tert-butyl ether, wash with 200ml of purified water, and concentrate the upper organic phase to dryness after liquid separation Using...

Embodiment 25

[0080] Add 30g (119mmol) ethyl 2,2-dimethyl-6-bromohexanoate into 200ml tetrahydrofuran, and add 12.08g (59.7mmol) diethyl 1,3-acetonedicarboxylate successively under stirring, 19g (137.5 mmol) potassium carbonate, 2g (12.0mmol) potassium iodide, warming up to reflux, after insulation for 100 hours, the system was cooled to room temperature, filtered, filter cake was rinsed with 20ml tetrahydrofuran, after the mother liquor was concentrated, 90ml ethanol was added, 120ml purified water, 21.3g (535mmol) sodium hydroxide, heated to reflux, kept reflux for 4 hours, after the NMR tracking reaction was completed, the system was concentrated to dryness, added 80ml of water to dissolve, extracted with 100ml methyl tert-butyl ether after dissolving, after liquid separation, Use 36% concentrated hydrochloric acid to adjust the pH of the water phase to 1-2, control the temperature of the system at 0-10°C throughout the process, stir for 15 minutes, filter, and recrystallize the filter ca...

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Abstract

The invention belongs to the field of chemical synthesis, and relates to a compound with a structural formula as described in the specification. In the structural formula, R1, R2 and R3 are independently selected from C1-C6 alkyl groups, alkenyl groups and cycloalkyl groups respectively. The invention also provides a method for synthesizing 8-hydroxy-2,2,14,14-tetramethyl pentadecanedioic acid byusing the compound. The method has the advantages of short reaction steps, simplified operation and greatly reduced production cost; and the use of raw materials with high toxicity and danger is avoided, so the method is safer.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a compound and a method for synthesizing 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid. Background technique [0002] 8-Hydroxy-2,2,14,14-tetramethylpentadecanedioic acid (Bempedoic Acid), also known as ETC-1002, has the following structural formula: [0003] [0004] Bempedoic Acid, developed by Esperion Therapeutic Inc, is a novel inhibitor of ATP citrate lyase (ACL), which can reduce cholesterol biosynthesis and lower LDL-C levels by upregulating LDL receptors, and can be used to treat dyslipidemia and reduce the risk of other cardiovascular diseases. Compared with the currently widely used statins in clinical practice, the advantage of Bempedoic Acid is that it is better tolerated, and it can be used in combination with statins for the treatment of LDL-C that cannot be suppressed by existing methods. [0005] WO2004067489 reports that the synthetic route of Bempedo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C69/34C07C51/09C07C59/347C07C51/367C07C59/285C07C69/63
CPCC07C67/343C07C69/34C07C51/09C07C59/347C07C51/367C07C59/285C07C2601/14C07C69/63
Inventor 吕宏海郭万成李永刚南燕辉王国彬
Owner AURISCO PHARM(TIANJIN) INC
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