Cetilistat preparation method

A technology of new lisstat and synthesis method, which is applied in the field of preparation of new lisstat, a drug for the treatment of obesity and its complications, can solve the problems of high equipment requirements, complicated operation, high risk factor, etc., and achieve economical and safe Improvement, post-processing is easy to operate, and the effect of low equipment requirements

Active Publication Date: 2017-02-01
LUNAN PHARMA GROUP CORPORATION
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AI-Extracted Technical Summary

Problems solved by technology

[0015] In the synthetic route of 2-hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-ketone disclosed in CN1785967A, the steps are more loaded down with trivial details, and in the synthesis of intermediates, a drastic Poisonous phosge...
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Method used

Adopt pyridine in prior art as acid-binding agent and solvent, and be sulfonylation reagent with sulfonyl chloride used in the present invention, although react...
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Abstract

The invention discloses a cetilistat preparation method. The cetilistat preparation method comprises the steps of allowing 2-amino-5-methyl benzoic acid to react with cetyl chloroformate and sulfonyl chloride one after another in alcohols solvent under the presence of acid binding agents to obtain cetilistat. The non-toxic and cheap ethanol is used as a reaction solvent, the preparation method is more economical, and the security of the preparation method is greatly improved. The sulfonyl chloride reacting fast is used as a cyclization reagent, reaction time is thus obviously reduced; postprocessing is simple and easy to operate, the requirement on equipment is low, and the industrial production of the cetilistat is facilitated.

Application Domain

Organic chemistry

Technology Topic

SolventSulfonyl chloride +7

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  • Cetilistat preparation method
  • Cetilistat preparation method
  • Cetilistat preparation method

Examples

  • Experimental program(7)

Example Embodiment

[0034] Example 1
[0035] Weigh 12g (79.39mmol, 1.0eq) of 2-amino-5-methylbenzoic acid, 10.03ml (91.31mmol, 1.15eq) of N-methylmorpholine and join in a 500ml three-necked flask, add 100ml absolute ethanol, Stir to dissolve, and cool down in an ice bath. When the temperature of the reaction system is 5°C, start to slowly add 29.05g (95.27mmol, 1.2eq) of hexadecyl chloroformate dropwise, and control the temperature not to exceed 10°C. The dropwise addition is completed in about 30 minutes , a large number of light yellow solids are formed in the system, slowly raise the temperature to 30°C, keep the temperature for 30 minutes, then cool down to 0-5°C, start to slowly add 18.12ml (223.86mmol, 3.0eq) of sulfuryl chloride dropwise, and the dropwise addition is completed in about 20 minutes , during the dropping process, the temperature is controlled not to exceed 10°C. After the dropping is completed, continue to stir and react for 30 minutes, then slowly raise the temperature to 25°, and keep the temperature for 1 hour. After 20 minutes, filter with suction, wash with 60ml of water, wash the filter cake with 30ml of absolute ethanol, drain it, put the filter cake in a vacuum oven at 35°C and dry it for 6 hours, with a yield of 92%.

Example Embodiment

[0036] Example 2
[0037] Weigh 12g (79.39mmol, 1.0eq) of 2-amino-5-methylbenzoic acid, 10.03ml (91.31mmol, 1.15eq) of N-methylmorpholine and join in a 500ml three-necked flask, add 100ml of anhydrous methanol, Stir to dissolve, and cool down in an ice bath. When the temperature of the reaction system is 5°C, start to slowly add 29.05g (95.27mmol, 1.2eq) of hexadecyl chloroformate dropwise, and control the temperature not to exceed 10°C. The dropwise addition is completed in about 30 minutes , a large number of light yellow solids are formed in the system, slowly raise the temperature to 30°C, keep the temperature for 30 minutes, then cool down to 0-5°C, start to slowly add 18.12ml (223.86mmol, 3.0eq) of sulfuryl chloride dropwise, and the dropwise addition is completed in about 20 minutes , during the dropping process, the temperature is controlled not to exceed 10°C. After the dropping is completed, continue to stir and react for 30 minutes, then slowly raise the temperature to 25°, and keep the temperature for 1 hour. After 20 minutes, filter with suction, wash with 60ml of water, wash the filter cake with 30ml of absolute ethanol, drain it, put the filter cake in a vacuum oven at 35°C and dry it for 6 hours, with a yield of 88%.

Example Embodiment

[0038] Example 3
[0039] Weigh 12g (79.39mmol, 1.0eq) of 2-amino-5-methylbenzoic acid, 10.03ml (91.31mmol, 1.15eq) of N-methylmorpholine and join in a 500ml three-necked flask, add 100ml isopropanol, Stir to dissolve, and cool down in an ice bath. When the temperature of the reaction system is 5°C, start to slowly add 29.05g (95.27mmol, 1.2eq) of hexadecyl chloroformate dropwise, and control the temperature not to exceed 10°C. The dropwise addition is completed in about 30 minutes , a large number of light yellow solids are formed in the system, slowly raise the temperature to 30°C, keep the temperature for 30 minutes, then cool down to 0-5°C, start to slowly add 18.12ml (223.86mmol, 3.0eq) of sulfuryl chloride dropwise, and the dropwise addition is completed in about 20 minutes , during the dropping process, the temperature is controlled not to exceed 10°C. After the dropping is completed, continue to stir and react for 30 minutes, then slowly raise the temperature to 25°, and keep the temperature for 1 hour. After 20 minutes, filter with suction, wash with 60ml of water, wash the filter cake with 30ml of absolute ethanol, drain it, put the filter cake in a vacuum oven at 35°C and dry it for 6 hours, the yield is 84%.

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