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Recycling method of acetyl Meldrum's acid derivative degradation waste

A technology of Acetyl McBurney's Acid and its derivatives, which is applied in the field of resource recycling, and can solve problems such as environmental pollution, the inability to use sitagliptin API production, and the increase in the production cost of sitagliptin API

Pending Publication Date: 2021-06-29
TAIZHOU BIOMEDICAL & CHEM IND RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the production process of the sitagliptin bulk drug, the acetylmycorrhizal acid derivative (referred to as compound II) of the structure shown in formula II usually needs to be stored according to the actual progress of production, however, due to the poor stability of compound II , it is easily affected by factors such as humidity and temperature in the production area during storage, such as being affected by high temperature weather in summer, and degrades, resulting in the loss of compound II. After compound II is degraded, its chemical structure and physical and chemical properties have been changed. It has changed and cannot be applied to the production of sitagliptin API, and becomes waste to be treated in the production process of sitagliptin API, which leads to an increase in the production cost of sitagliptin API, and there is also the problem of environmental pollution

Method used

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  • Recycling method of acetyl Meldrum's acid derivative degradation waste
  • Recycling method of acetyl Meldrum's acid derivative degradation waste
  • Recycling method of acetyl Meldrum's acid derivative degradation waste

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Take 8.00g of the oily waste produced by the degradation of Compound II and preheat at 60°C for 30min to obtain a preheated material; dissolve the preheated material in 80mL of methanol and heat to reflux under stirring (system temperature is 105~110 ​​℃), maintain reflux state and carry out alcoholysis reaction 60h (TLC monitors reaction process); Heated to 55-60°C under stirring conditions, and carried out ammonolysis reaction for 16 hours (monitoring the reaction process by TLC); after the reaction, the obtained system was cooled to room temperature, and the solvent was recovered by distillation under reduced pressure, and the residue was dissolved in 60 mL of ethyl acetate, The resulting mixture was washed 3 times with water (80mL×3), the organic layer was separated and the solvent was recovered by distillation under reduced pressure, the residue was dissolved in 20mL of toluene, and 8mL of acetic anhydride was added, and the resulting system was heated to reflux (th...

Embodiment 2

[0060] Take 12.00g of the oily waste produced by the degradation of Compound II and preheat it at 60°C for 30min to obtain the preheated material; dissolve the preheated material in 80mL of methanol and heat to reflux under stirring (the system temperature is 105~110 ​​℃), maintain reflux state and carry out alcoholysis reaction 72h (TLC monitors reaction process); Heated to 55-60°C under stirring conditions, and carried out ammonolysis reaction for 24 hours (monitoring the reaction process by TLC); after the reaction, the obtained system was cooled to room temperature, and the solvent was recovered by distillation under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate, The resulting mixture was washed 3 times with water (80mL×3), the organic layer was separated and the solvent was recovered by distillation under reduced pressure, the residue was dissolved in 30mL of toluene, and 10mL of acetic anhydride was added, and the resulting system was heated t...

Embodiment 3

[0063]Get 16.00g of the oily waste produced by the degradation of Compound II and preheat at 60°C for 30min to obtain a preheated material; dissolve the preheated material in 80mL of ethanol and heat to reflux under stirring (system temperature is 105~110 ​​℃), maintain reflux state and carry out alcoholysis reaction 60h (TLC monitors reaction process); Heated to 55-60°C under stirring conditions, and carried out ammonolysis reaction for 24 hours (monitoring the reaction process by TLC); after the reaction, the obtained system was cooled to room temperature, and the solvent was recovered by distillation under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate, The resulting mixture was washed 3 times with water (120mL×3), the organic layer was separated and the solvent was recovered by distillation under reduced pressure, the residue was dissolved in 30mL of toluene, and 10mL of acetic anhydride was added, and the resulting system was heated to reflux (t...

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Abstract

The invention provides a recycling method of acetyl Meldrum's acid derivative degradation waste, and belongs to the technical field of resource reutilization. According to the method disclosed by the invention, acetyl Meldrum's acid derivative degradation waste is subjected to preheating treatment, alcoholysis reaction, ammonolysis reaction, acetylation reaction and purification treatment, the main components in theacetyl Meldrum's acid derivative degradation waste are converted, and a recovery product is finally obtained and can be used as an important intermediate in a sitagliptin production process, so that waste resource reutilization in the production process of the sitagliptin bulk drug is realized, economic loss caused by degradation of the acetyl Meldrum's acid derivative in the production process of the sitagliptin bulk drug is reduced, the problem of environmental pollution caused by degradation of the acetyl Meldrum's acid derivative in the production process of the sitagliptin bulk drug is eliminated, and the sustainable development of a sitagliptin raw material medicine green pharmaceutical process is promoted.

Description

technical field [0001] The invention relates to the technical field of resource recycling, in particular to a method for recycling wastes degraded by acetyl-Merfurer's acid derivatives. Background technique [0002] Sitagliptin was developed by Merck, its phosphate salt (trade name Januvia) as the first DPP-4 inhibitor, clinically used in the treatment of type II diabetes, the drug can also be combined with other drugs (such as metformin), combined Treatment of type II diabetes. The chemical name of sitagliptin is (3R)-3-amino-1-[3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4 ,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one has the structure shown in formula I: [0003] [0004] Merck & Co., Ltd. has disclosed 5-(1-hydroxyl-2-(2,4,5-trifluorophenyl) ethylidene)-2,2-dimethyl-1,3-bis Oxyheterocycle-4,6-diketone (structural formula shown in formula II) is a key intermediate, a method for synthesizing sitagliptin bulk drug through multi-step reactions (Jour...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/47C07C231/02C07C231/24
CPCC07C231/02C07C231/24C07C227/08C07C67/28C07C233/47C07C229/34C07C69/732Y02P20/582
Inventor 韩得满程格武承林
Owner TAIZHOU BIOMEDICAL & CHEM IND RES INST CO LTD
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