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Hydrochlorides of dipeptide compounds and preparation method thereof

A compound and hydrochloride technology, applied in the field of chemical synthesis, can solve the problems of easy moisture absorption, not particularly good properties, low product purity, etc., and achieve the effect that it is not easy to absorb moisture

Inactive Publication Date: 2016-09-28
湖北华世通生物医药科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, dipeptides and their analogs have been used more and more in the pharmaceutical and biological industries, and their demand has also increased year by year. However, the products currently prepared have low purity, and their properties are not particularly good, and they are easily absorbed. tide, unstable
In order to facilitate long-term placement and transportation, technicians usually choose to make hydrochloride, but most hydrochloride compounds tend to adsorb more hydrochloric acid on the surface, resulting in changes in the isoelectric point of dipeptide or polypeptide amino acids, making it impossible to Normal precipitation from the reaction solution, so there is no solid dipeptide compound hydrochloride product in the prior art
This technical problem has also been difficult to solve

Method used

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  • Hydrochlorides of dipeptide compounds and preparation method thereof
  • Hydrochlorides of dipeptide compounds and preparation method thereof
  • Hydrochlorides of dipeptide compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] a. Synthesis of crude solution of compound 1

[0062] Add 42.0 g (0.1 mol) of the compound shown in Formula 2 and 168.0 g (2.0 mol) of dichloromethane into a 2000 mL reaction flask, and stir to dissolve at room temperature. Mole / liter of hydrogen chloride dioxane solution 150.0ml (0.6mol), control the temperature at 5-10°C, stir for 3.0 hours, HPLC monitors the remaining 0.07% of the raw material, the reaction is qualified, add 840.0 methyl tert-butyl ether to the reaction solution g (9.5mol), stirred for 10 minutes, poured off the supernatant, added 504.0g (5.7mol) of dioxane at 0-5°C, stirred for 10 minutes, then added 504.0g of methyl tert-butyl ether ( 5.7 mol), stirred at 0-5°C for 30 minutes, and suction filtered to obtain 34.1 g of a crude product with a purity of 98.8% and a yield of 95.7%. b, the purification of formula 1 finished product

[0063] Add 504.0 g (7.0 mol) of tetrahydrofuran to the crude product obtained above, stir at room temperature to dissolv...

Embodiment 2

[0065] a, the synthesis of compound crude product solution shown in formula 1

[0066] Add 42.0g (0.1mol) of the compound shown in formula 2 and 420.0g (4.9mol) of dichloromethane into a 2000mL reaction bottle, stir and dissolve at room temperature, after the reaction solution is dissolved and clarified, cool down to -2~5°C, and start adding dropwise 125.0ml (0.5mol) of 4 mol / liter hydrogen chloride dioxane solution, control the temperature at 5-10°C, stir for 3.0 hours, HPLC monitors the remaining 1.8% of raw materials, and the reaction is qualified, and methyl tert-butyl ether is added to the reaction solution 840.0g (9.5mol), stirred for 10 minutes, poured off the supernatant, added 504.0g (5.7mol) of dioxane at 0-5°C, stirred for 10 minutes, then added 504.0g of methyl tert-butyl ether (5.7mol), stirred at 0-5°C for 30 minutes, and filtered with suction to obtain 30.1 g of crude product with a purity of 96.8% and a yield of 84.2%.

[0067] b. Purification of the finished ...

Embodiment 3

[0070] a, the synthesis of compound crude product solution shown in formula 1

[0071] Add 42.0g (0.1mol) of the compound shown in Formula 2 and 168.0g (2.0mol) of dichloromethane into a 2000mL reaction flask, stir and dissolve at room temperature, after the reaction solution is dissolved and clarified, cool down to 5-10°C, and start to add 2 Mole / liter hydrogen chloride dioxane solution 300.0ml (0.6mol), control the temperature at 5-10°C, stir for 3.0 hours, HPLC monitors the remaining 0.3% of raw materials, the reaction is qualified, add 840.0g of methyl tert-butyl ether to the reaction solution (9.5mol), stirred for 10 minutes, poured off the supernatant, added 504.0g (5.7mol) of dioxane at 5-10°C, stirred for 10 minutes, then added 504.0g (5.7mol) of methyl tert-butyl ether mol), stirred at 5-10° C. for 30 minutes, and suction filtered to obtain 32.1 g of a crude product with a purity of 98.0% and a yield of 90.1%.

[0072] b. Purification of the finished product of Compo...

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Abstract

The invention provides hydrochlorides of dipeptide compounds and a preparation method thereof. The method comprises the following steps: a first organic solvent is used for dissolving a compound shown in a formula 2; dissolving liquid of the compound shown in the formula 2 and a second organic solvent of hydrogen chloride are contacted, so that a first crude product of a compound shown in a formula 1 is obtained. The hydrochlorides of dipeptide compounds are precipitated from the solution by the method, and the product has the advantages of high purity, good properties and stability, and transport and long-time storage convenience.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular, the invention relates to a hydrochloride of dipeptide compounds and a preparation method thereof. Background technique [0002] In recent years, dipeptides and their analogs have been used more and more in the pharmaceutical and biological industries, and their demand has also increased year by year. However, the products currently prepared have low purity, and their properties are not particularly good, and they are easily absorbed. Tide, unstable. In order to facilitate long-term placement and transportation, technicians usually choose to make hydrochloride, but most hydrochloride compounds tend to adsorb more hydrochloric acid on the surface, resulting in changes in the isoelectric point of dipeptide or polypeptide amino acids, making it impossible to It normally separates out from the reaction solution, so there is no solid dipeptide compound hydrochloride product in the prio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/08
CPCC07D207/08
Inventor 王念李涛
Owner 湖北华世通生物医药科技有限公司
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