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A technology of risstat and compound, which is applied in the field of synthesizing cetiristat, can solve the problems of high cost, difficult reaction conditions, and low yield
Inactive Publication Date: 2014-07-23
CHONGQING TOPTECH PHARMA TECH
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Problems solved by technology
[0013] The present invention solves the problems of low yield and high cost in the current method of preparing cetilistat (hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-one, cetilistat) , Reaction conditions are not easy for industrial production, etc., providing a new synthetic route and corresponding preparation method
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Embodiment 1
[0061] Put compound A (45.3g, 0.3mol) into a 1L reaction flask, add 500ml of methanol, add 30ml of concentrated sulfuric acid dropwise under stirring, stir overnight at room temperature, concentrate and recover most of the methanol, add 200ml of acetone, and stir in an ice bath for 2h. Suction filtration and drying gave 73.4 g of 2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate, with a yield of 93%.
Embodiment 2
[0063] Put compound A hydrochloride (56.3g, 0.3mol) into a 1L reaction flask, add 600ml tetrahydrofuran and tert-butanol (26.7g, 0.36mol), add DCC (61.9g, 0.3mol) in batches under stirring, and Stir for 2h, then add DMPA (0.5g), stir overnight, concentrate and recover most of THF, add 600ml ethyl acetate and 30g sodium bicarbonate, stir for 1h, filter with suction, the filtrate is sequentially washed with 1% acetic acid solution, water and saturated saline Fully stirred, washed, separated, concentrated under reduced pressure to a slurry, added 500ml of petroleum ether, stirred for 2h in an ice bath, filtered with suction, and dried to obtain 55.9g of tert-butyl 2-amino-5-methylbenzoate. The yield was 90%.
Embodiment 3
[0065] Put compound A (45.3g, 0.3mol) into a 1L reaction flask, add 500ml of toluene and thionyl chloride (53.6g, 0.45mol), heat up to reflux, stir for 2h, cool down to room temperature, drop benzyl alcohol (43.2g , 0.4mol), stirred overnight at room temperature, concentrated most of the solvent under reduced pressure to form a slurry, stirred for 2h under ice bath, filtered with suction, and dried to obtain 79.2g of benzyl 2-amino-5-methylbenzoate hydrochloride , The yield is 95%.
[0066] Preparation of Compound C:
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Abstract
The invention discloses a method for preparing cetilistat, which belongs to the technical field of the medicine preparation method, and is used for solving the problems of high three wastes, low yield and high cost in the current preparation method. The method comprises the following steps: 1)esterifying a compound A(2-amino-5-methyl benzoic acid) or its salt; 2) acylating an esterification object in the step 1) and chloroformic acid n-cetanol ester; 3)removing ester group of the compound obtained in the step 2) to obtain 2-(cetane carbonyl oxygen)amino-5-methyl benzoic acid; and 4)cyclizing the compound in the step 3) to obtain the target products. By improving the production steps, the invention provides the synthetic method with simple operation, high efficiency, and convenient industrial production for the cetilistat product.
Description
technical field [0001] The invention belongs to the technical field of preparation methods of medicines, in particular, it is a method for synthesizing cetiristat product which is easy to operate, highly efficient and convenient for industrial production. Background technique [0002] Cetilistat (2-hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-one, cetilistat) is a long-acting and potent drug developed by Alizyme Specific gastrointestinal lipase inhibitors form covalent bonds with the active serine sites of gastric lipase and pancreatic lipase in the lumen of the stomach and small intestine to inactivate the enzymes, thereby achieving the therapeutic effect of reducing calorie intake and controlling body weight. The biggest advantage of this drug is that it does not act on the nervous system, does not affect other enzyme activities in the gastrointestinal tract, and is safer than the current similar drug orlistat. Its structural formula is as follows: [0003] [0004] In t...
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