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Application of asymmetric hydrogenation reaction in evogliptin synthesis

A hydrogenation reaction, asymmetric technology, applied in the direction of organic chemistry, can solve the problems of low product yield, high cost, poor quality, etc., and achieve the effect of simple synthesis method, good product quality and low cost

Inactive Publication Date: 2017-11-03
SUZHOU XINEN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the prior art, the synthesis process of epagliptin is often more complicated, the cost is higher, and there are also defects of low product yield and poor quality, which cannot be suitable for industrialized large-scale production

Method used

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  • Application of asymmetric hydrogenation reaction in evogliptin synthesis

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Embodiment

[0027] Preparation of compound (4)

[0028] Add 20 L of reaction solvent anhydrous dichloromethane and 2.5 kg (11 mol) of compound (2) into a 50L reaction kettle at 0°C, then slowly add 1.5 kg (11 mol) of oxalyl chloride (3 hours), and keep the temperature At about 0°C, TLC followed the reaction after the addition, and the reaction ended after 3 hours.

[0029] Add 10 L of reaction solvent anhydrous dichloromethane and 1.86kg (10 mol) of compound (3) to another 50L reaction kettle at 0°C, then add 1.11 kg (11 mol) of triethylamine, and then slowly add the above Acyl chloride, keep the temperature at about 0°C, follow the reaction by TLC after the addition is complete, add the reaction solution to 20L 5% sodium bicarbonate aqueous solution after 3 hours, separate the liquid, and concentrate the organic phase under reduced pressure to obtain compound (4) 3.76 kg (9.39 mol), the yield was 93.9%. HPLC detection purity: 97.8%.

[0030] 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.47 – 7...

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Abstract

The invention provides a synthesis method of a compound evogliptin of a formula (1). Compounds of a formula (2) and a formula (3) are taken as starting materials and are subjected to a series of reactions as follows to finally prepare the compound of the formula (1), namely the evogliptin (formulae are shown in the description). Compared with the prior art with the defects of multiple synthesis steps of the evogliptin and a complex synthesis process, the synthesis method provided by the invention is simple and practicable, the cost is lower, the yield is higher, the product quality is better, and the synthesis method is suitable for large scale industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing epagliptin, which belongs to the technical field of drug synthesis. Background technique [0002] Elogliptin (generic name: EVOGLIPTIN, trade name Suganon), chemical name: (R)-4-((R)-3-amino-4-(2,4,5-trifluorophenyl) butyl Acyl)-3-(tert-butanol ether methyl)piperazin-2-one. The molecular weight of Elogliptin: 401.42; CAS registration number: 1222102-29-5; the structural formula is shown in Formula 1: [0003] [0004] Formula 1 [0005] Elogliptin was developed by Dong-A Pharmaceutical Company in South Korea. On October 2, 2015, it was approved by the Korean Ministry of Food and Drug Safety (MFDS) for the treatment of type 2 diabetes in South Korea. Ilogliptin is a DPP-4 inhibitor drug for the treatment of type 2 diabetes. Dosage specification: Elogliptin 5mg / tablet. [0006] prior art literature [0007] Non-patent literature: 1: Lab. Invest., 2016, 96, 5, P547-P560; Non-patent literature 2: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/08
CPCC07D241/08
Inventor 王保安
Owner SUZHOU XINEN PHARMA