Orlistat preparation method

An orlistat and compound technology, applied in the field of pharmaceutical preparation, can solve the problems of increasing the production cost of β-hydroxyester, low economic and practical value, long synthesis route, etc., and achieve high practical value, low price, and reduced production cost. Effect

Inactive Publication Date: 2006-05-03
ARGUS PHARMA
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Problems solved by technology

However, the synthetic route provided by this patent is relatively long (twelve-step reaction), which increases the production cost of β-hydroxyester (an important intermediate for the synthesis of orlistat)
In addition, the reagents used to control the chirality of the 5-hydroxyl group are relatively expensive and have low economic and practical value.

Method used

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Examples

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Embodiment 1

[0043] The first step of (5R)-5-hydroxy-3-oxocetanoic acid methyl ester (IV) preparation

[0044] A solution of (S)-(-)-BINOL (458 mg, 1.6 mmol) in THF was added to Ti(OPr-i) under nitrogen 4 (455mg, 1.6mmol). The solution was stirred at room temperature for 20 minutes, then lauraldehyde (14.75g, 80mmol), lithium chloride (1.10g, 0.026mol) and N,N,N',N'-tetramethylethylenediamine (6.14g , 0.053mol) was added. The mixture was stirred at room temperature for 20 minutes, and then 1,3-bis(trimethylsilyloxy)-1-methoxy-1,3-butadiene (48.7g, 187mmol) was added dropwise. Stir for 4 hours. Add NaHCO after the reaction 3 aqueous solution, and the organic layer was treated with ethyl acetate to obtain compound formula (IV).

[0045] The second step (5R)-5-p-methoxybenzyloxy-3-oxocetanoic acid methyl ester, prepared as formula (V)

[0046] A solution of 4-methoxybenzyl alcohol (5.18 g, 37.5 mmol) in ether was added to NaH (90 mg, 3.75 mmol, 60% mineral / oil) in ether at room temperat...

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Abstract

The invention relates to a preparation method for oleanstada, which comprises: on catalyst action, using enolsiliconether and lauraldehyde to condense directly and obtain chiral hydroxyl hexadeketo ester; after eight steps contained protecting hydroxyl group, reducing and cyclization, obtaining the objective product with chemical formula as (I) for efficient fat-reducing. This method needs low cost.

Description

technical field [0001] The invention relates to a preparation method of orlistat, which belongs to the technical field of medicine preparation. Background technique [0002] Orlistat is currently the only lipase inhibitor in weight-loss drugs. Its main function is to selectively inhibit the activity of lipase in the gastrointestinal tract, and achieve the goal of weight loss by blocking about 30% of dietary fat from being absorbed by the body. Unlike other weight-loss drugs, its biggest advantage is that it does not act on the nervous system, does not enter the blood, and does not suppress appetite. This drug has been listed in more than 100 countries around the world, accounting for 2 / 3 of the world's weight-loss drug market. [0003] Chinese patent ZL97109732.1 provides a method for producing lipostatin by fermentation. Lipostatin can be isolated from the culture medium and can be reduced to tetrahydrolipstatin. The lipostatin-producing microorg...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/12
Inventor 陈卫平杨琍苹
Owner ARGUS PHARMA
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