Synthetic method for 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid

A technology of pentadecanedioic acid and pentadecanedioic acid salt, applied in chemical instruments and methods, carboxylate preparation, carboxylate preparation and other directions, can solve the problem of not easy industrial production, incomplete reaction, high risk problems, to achieve the effect of reducing cost input, reducing risk, and simplifying operation

Pending Publication Date: 2019-05-07
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses NaBH 4 When used as a reducing agent, the amount used is more than ten times that of the substrate, and the substrate is still incompletely reacted after more than ten hours. In the subsequent acid addition process, a large amount of hydrogen will be generated, which is prone to the risk of flushing
The synthetic method is complicated, dangerous, and costly, and is not easy for industrial production

Method used

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  • Synthetic method for 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid
  • Synthetic method for 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Pour 5.0g (14.6mmol) of 8-keto-2,2,14,14-tetramethyl-pentadecanedioic acid into 50ml of purified water, add 1.46g (36.5mmol) of sodium hydroxide, and keep stirring until all Dissolve, react at 20°C for 30 minutes, add 0.55 g (14.6 mmol) of sodium borohydride to the reaction solution, continue the reaction for 4 hours, and spot the plate with TLC (developing agent: ethyl acetate: n-hexane: acetic acid = 1:5 :0.3) The reaction is complete. Add concentrated hydrochloric acid to the reaction solution, adjust the pH to 1, stir for 10 minutes, add 60ml of methyl tert-butyl ether for extraction three times, combine the organic layers, wash the solution with 60ml of purified water for three times, separate the organic layer, Wash once with 60ml of saturated brine, dry over anhydrous sodium sulfate for 2 hours, filter and evaporate the organic layer to dryness to obtain a white solid which is 8-hydroxy-2,2,14,14-tetramethyl-pentadecanedioic acid, Yield 97.9%, purity 99.3%.

Embodiment 2

[0027] Pour 5.0g (14.6mmol) of 8-keto-2,2,14,14-tetramethyl-pentadecanedioic acid into 75ml of purified water, add 2.46g (43.8mmol) of potassium hydroxide, and keep stirring until all Dissolved, reacted for 30 minutes at 25°C, added 0.66 g (17.5 mmol) of sodium borohydride to the reaction solution, continued the reaction for 4 hours, and spotted the plate with TLC (developing agent: ethyl acetate: n-hexane: acetic acid = 1:5 :0.3) The reaction is complete. Add conc Wash once with 60ml of salt water, dry over anhydrous sodium sulfate for 2 hours, filter and evaporate the organic layer to dryness to obtain a white solid, which is 8-hydroxy-2,2,14,14-tetramethyl-pentadecanedioic acid. Yield 96.3%, purity 98.5%.

Embodiment 3

[0029] Pour 5.0g (14.6mmol) of 8-keto-2,2,14,14-tetramethyl-pentadecanedioic acid into 60ml of purified water, add 2.16g (29.2mmol) of calcium hydroxide, and keep stirring until all Dissolve, react at 20°C for 30 minutes, add 0.55 g (14.6 mmol) of sodium borohydride to the reaction solution, continue the reaction for 4 hours, and spot the plate with TLC (developing agent: ethyl acetate: n-hexane: acetic acid = 1:5 :0.3) The reaction is complete. Add concentrated hydrochloric acid to the reaction solution, adjust the pH to 1, stir for 10 minutes, add 60ml of methyl tert-butyl ether for extraction three times, combine the organic layers, wash the solution with 60ml of purified water for three times, separate the organic layer, Wash once with 60ml of saturated brine, dry over anhydrous sodium sulfate for 2 hours, filter and evaporate the organic layer to dryness to obtain a white solid, which is 8-hydroxy-2,2,14,14-tetramethyl-pentadecanedioic acid , yield 95.9%, purity 98.2%. ...

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Abstract

The invention belongs to the technical field of medicines, and specifically provides a synthetic method for 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid. The synthetic method comprises the following steps: (1) pouring 8-keto-2,2,14,14-tetramethyl-pentadecanedioic acid into purified water, and adding a proper amount of alkali until the 8-keto-2,2,14,14-tetramethyl-pentadecanedioic acid iscompletely dissolved so as to obtain 8-keto-2,2,14,14-tetramethyl-pentadecanediate; (2) adding sodium borohydride into an above-mentioned reaction solution, and carrying out a carbonyl reduction reaction under the condition of 20 to 25 DEG C so as to obtain 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanediate; and (3) adding concentrated hydrochloric acid into an above-mentioned reaction solution until the pH value of the reaction solution is adjusted to 1 to 3 so as to generate the 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid. The synthetic method provided by the invention reduces theusage amount of the sodium borohydride, decreases the dangerousness of a reaction, simplifies operation, reduces the cost input amounts of a solvent and raw materials, and is applicable to industrialproduction.

Description

technical field [0001] The invention belongs to the field of pharmaceutical synthesis and relates to a new synthesis method of compound 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid. Background technique [0002] At present, the clinically used lipid-lowering drugs mainly include the following: statins, fibrates, nicotinic acid, cholesterol absorption inhibitors, and bile acid sequestrants. Both domestic and foreign blood lipid prevention and control guidelines clearly point out that low-density lipoprotein cholesterol (LDL-C) is the primary treatment target. Statins are hydroxymethylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, which are clinically effective drugs for lowering LDL-C and reducing the risk of cardiovascular diseases. However, many people at high risk of cardiovascular disease cannot reach the target value of LDL-C after taking statins. It needs to be increased to several times the conventional dose to greatly reduce the level of LDL-C, but the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/367C07C51/02C07C59/245C07C51/41C07C59/347
Inventor 张贵民段良兴王军
Owner LUNAN PHARMA GROUP CORPORATION
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