A kind of synthetic method of trientine hydrochloride

A synthesis method, hydrochloric acid technology, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve the problems of poor molecular economy, expensive synthetic raw materials, unsuitable for industrial production, etc., and achieve short and safe synthesis routes Good sex, significant social and economic benefits

Active Publication Date: 2020-12-04
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] This method starts with 2,2-(2,2-(ethane-1,2-diyl-bisbenzyl-bis(ethane-2,1-diyl))diisoindole-1,3- Diketone is the raw material, the synthetic raw material is relatively special and expensive, the molecular economy in the synthetic process is poor, and it is still not suitable for industrial production

Method used

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  • A kind of synthetic method of trientine hydrochloride
  • A kind of synthetic method of trientine hydrochloride
  • A kind of synthetic method of trientine hydrochloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Step 1 Preparation of Intermediate I

[0044] The content of each component is: the molar ratio of ethylenediamine and di-tert-butyl dicarbonate is 2:1.

[0045] The preparation method is: in a 1L round bottom flask, add (2.7mL, 40mmol) ethylenediamine and 400mL chloroform, stir in an ice bath for 0.5h, then add (4.4g, 20mmol) Boc 2 O, the reaction solution was stirred at room temperature for 16 h and washed three times with 200 mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain a colorless transparent liquid (intermediate I), with a yield of 98%. 1 H-NMR (400MHz, CDCl 3 )δ5.39(1H,s),3.05(2H,d,J=4.8Hz),2.64(2H,d,J=5.2Hz),1.29(9H,s),1.08(2H,s). 13 C-NMR (400MHz, CDCl 3 ) δ 156.2, 78.8, 43.3, 41.7, 28.3.

[0046] Step 2 Preparation of Intermediate II

[0047] The content of each component is: the molar ratio of intermediate I to 1,2-dibromoethane is 2:1.

[0048...

Embodiment 2

[0053] Step 1 Preparation of Intermediate I

[0054] The content of each component is: the molar ratio of ethylenediamine and di-tert-butyl dicarbonate is 8:1.

[0055] The preparation method is: in a 1L round bottom flask, add (5.4mL, 80mmol) ethylenediamine and 400mL chloroform, stir in an ice bath for 0.3h, then add (2.2g, 10mmol) Boc 2 O, the reaction solution was stirred at room temperature for 13 h, washed three times with 200 mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a colorless transparent liquid (Intermediate I), with a yield of 49%.

[0056] Step 2 Preparation of Intermediate II

[0057] The content of each component is: the molar ratio of intermediate I to 1,2-dibromoethane is 4:1.

[0058] The preparation method is: in a 50mL round bottom flask, add 0.5g (3.12mmol) intermediate I, 0.15g (0.78mmol) 1,2-dibromoethane and 1.72g (12.48mmol) potassium carbonate, the...

Embodiment 3

[0063] Step 1 Preparation of Intermediate I

[0064] The content of each component is: the molar ratio of ethylenediamine and di-tert-butyl dicarbonate is 1:1.

[0065] The preparation method is: in a 1L round bottom flask, add (5.4mL, 80mmol) ethylenediamine and 400mL chloroform, stir in an ice bath for 0.8h, then add (17.4g, 80mmol) Boc 2 O, the reaction solution was stirred at room temperature for 20 h and washed three times with 200 mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain a colorless transparent liquid (Intermediate I), with a yield of 63%.

[0066] Step 2 Preparation of Intermediate II

[0067] The content of each component is: the molar ratio of intermediate I to 1,2-dibromoethane is 4:1.

[0068] The preparation method is: in a 50mL round bottom flask, add 2g (12.5mmol) intermediate I, 0.59g (3.12mmol) 1,2-dibromoethane and 1.73g (12.48mmol) potassium c...

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Abstract

The invention discloses a synthesis method of trientine dihydrochloride and belongs to the field of drug synthesis. The synthesis method of trientine dihydrochloride comprises the steps: carrying outa t-butyloxycarboryl protective reaction on ethanediamine serving as an initial raw material to prepare an intermediate I; carrying out condensation on the intermediate I serving as a raw material and1, 2-dibromoethane to prepare an intermediate II; and finally, carrying out deprotection on the intermediate II serving as a raw material to synthesize trientine dihydrochloride. The synthesis methoddisclosed by the invention is short in route, low in cost, high in yield and suitable for industrialized production of trientine dihydrochloride, and the product is easy to purify.

Description

technical field [0001] The invention belongs to the field of organic medicine synthesis, and in particular relates to a synthesis method of trientine hydrochloride. Background technique [0002] Trientine hydrochloride is a copper ion chelating agent, which acts like penicillamine and can be used to remove excess copper in the body. STD patients. There are many documents about the synthetic technique of trientine hydrochloride to report it, such as US4806519; US4550209; US4766247; CZ197093; RU2186761; Large loss, low product yield, difficult to control the purity of the product and other defects, or the use of chemical reagents that are difficult to handle and harmful to the human body, do not conform to the scientific concept of green chemistry. Its representative synthetic route is as follows; [0003] Route 1: [0004] [0005] The synthesis method has a relatively long synthetic route and excessive use of protecting groups, which is unfavorable for its industrial ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/62C07C211/14
CPCC07C209/62C07C269/04C07C269/06C07C211/14C07C271/20Y02P20/55
Inventor 陈景超樊保敏周永云樊瑞峰和晓波孙蔚青曾广智尹俊林林成源
Owner YUNNAN MINZU UNIV
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