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Method for synthesizing (R)-beta-hydroxytetradecanoate

A technology of hydroxytetradecanoate and -binap-rubr2, which is applied in the field of synthesizing -β-hydroxytetradecanoate, can solve the problems that patients are unbearable, natural products are difficult to obtain, and production costs are high, and achieves low cost, Reaction conditions are easy to achieve, avoiding the effect of acid-resistant equipment

Inactive Publication Date: 2013-03-20
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, orlistat is usually prepared from the natural product Lipstatin (Lipstatin). Since the natural product is not easy to obtain, the production cost of orlistat by this method is too high, which is difficult for patients to bear.

Method used

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  • Method for synthesizing (R)-beta-hydroxytetradecanoate
  • Method for synthesizing (R)-beta-hydroxytetradecanoate
  • Method for synthesizing (R)-beta-hydroxytetradecanoate

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Example 1 Preparation of (R)-β-hydroxytetradecanoic acid methyl ester, the compound of formula (I) (R=Me)

[0021] Proceed as follows:

[0022] (1) Under nitrogen protection, the improved chiral catalyst (R)-BINAP-RuBr 2 (0.05g) was transferred to a 2L round bottom flask, then degassed methanol (1200mL) and methyl β-carbonyltetradecanoate (III) (R=Me) (200g, 0.78mol) were added, and the reaction temperature was 40°C , the reaction time is 12 hours, and the reaction pressure is 0.1kg / cm 2 ; After the reaction, a brown solution was obtained.

[0023] (2) After replacing the nitrogen in the flask with hydrogen for three times, stir the solution vigorously, keep it warm at 40°C, and keep it at 0.1kg / cm 2 Hydrogenation was carried out at low temperature until the hydrogen was no longer consumed for about 12 hours; after the hydrogen in the flask was removed with nitrogen, the reaction solution was concentrated under reduced pressure, and then recrystallized with n-hexane ...

Embodiment 2

[0024] Example 2 Preparation of (R)-β-hydroxytetradecanoic acid methyl ester, the compound of formula (I) (R=Me)

[0025] Proceed as follows:

[0026] (1) Under nitrogen protection, the improved chiral catalyst (R)-BINAP-RuBr 2 (0.5g) was transferred to a 20L glass reactor, and then degassed methanol (12L) and methyl β-carbonyltetradecanoate (III) (R=Me) (2000g, 7.8mol) were added, and the reaction temperature was 50°C , the reaction time is 10 hours, and the reaction pressure is 0.15kg / cm 2 ; After the reaction, a brown solution was obtained.

[0027] (2) After replacing the nitrogen in the flask with hydrogen for three times, the solution was vigorously stirred, kept at 50°C, and heated at 0.15kg / cm 2 Hydrogenation was carried out at low temperature until the hydrogen was no longer consumed for about 10 hours; after the hydrogen in the flask was removed with nitrogen, the reaction solution was concentrated under reduced pressure, and then recrystallized with n-hexane to o...

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Abstract

The invention discloses a method for synthesizing (R)-beta-hydroxytetradecanoate, which comprises the following steps of: (1) in the presence of an improved chiral catalyst (R)-BINAP-RuBr2, dissolving a compound of formula (III) in a solvent and performing catalytic hydrogenation; and (2) after the reaction ends, replacing nitrogen with hydrogen, and performing hydrogenation under a pressure of 0.1-0.2kg / cm<2>; and performing reduced-pressure concentration on the reaction solution, and recrystallizing to obtain white solid crystals which are (R)-beta-hydroxymethyltetradecanoate. According to the method, the improved chiral catalyst (R)-BINAP-RuBr2 is innovatively used for catalytic synthesis of (R)-beta-hydroxytetradecanoate compounds; and by use of the catalyst, the compound shown as the formula (III) can be converted into a high-stereoselectivity (greater than 98.5%ee) compound shown as the formula (I) under a relatively low pressure (0.01-6kg / cm<2>), and the use of high-pressure hydrogenation equipment and acid-resistant equipment is avoided. The method disclosed by the invention has the advantages of low cost, high yield, easy implementation of reaction conditions, adaptability to large-scale industrial production of compounds shown as the formula (I), and the like.

Description

technical field [0001] The invention relates to a method for synthesizing (R)-beta-hydroxy myristate. Background technique [0002] With the improvement of people's material living standards and unreasonable diet structure, the number of obese people is increasing year by year. Because obesity may induce or aggravate diabetes, fatty liver, cardiovascular and cerebrovascular system diseases, etc., obesity has become a serious hazard to human beings. One of the diseases of health. At present, the weight loss drug widely used clinically mainly includes Orlistat (Orlistat). Orlistat (Orlistat) is a long-acting and potent specific inhibitor of gastric lipase and pancreatic lipase, which can be covalently bound to the active serine residues of gastric lipase and pancreatic lipase in the gastrointestinal tract Inactivate the enzyme, thereby inhibiting the hydrolysis and absorption of about 30% of the fat in the food, so as to achieve the purpose of reducing the patient's weight. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/675C07C67/31
Inventor 孙彬彭立增
Owner SHANDONG NORMAL UNIV
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