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n-(2,2-dimethoxyethyl)-2-(1h-tetrazol-1-yl)amide and preparation method thereof
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A technology of dimethoxyethyl and tetrazolium, applied in organic chemistry and other directions, can solve problems such as instability, and achieve the effects of stable quality, mild reaction conditions and simple operation
Active Publication Date: 2017-10-17
GUANGZHOU BAIYUSN TIANXIN PHARMA
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[0003] In the impurity profile research of cefazolin sodium and cefazolin sodium pentahydrate raw materials and injections, we found that: cefazolin impurity B is N-(2,2-dihydroxyethyl)-2-(1H-tetra Azol-1-yl) amides can be observed by alkaline hydrolysis of cefazolin (HPLC method), but cannot be obtained by conventional methods such as preparation of liquid phase, extraction or precipitation separation, probably because the impurity is easy to form an acetal structure and unstable
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Embodiment 1
[0025] Example 1 Preparation of Compound I
[0026] Add 20 g of tetrazolium acetic acid into 160 ml of dichloromethane, cool down to below -15°C while stirring, add 24 ml of triethylamine dropwise, and stir until dissolved. After 19ml of pivaloyl chloride was added dropwise, 13.4ml of aminoacetaldehyde dimethyl acetal was added dropwise, and triethylamine was added dropwise to keep the pH at 7.0-8.0, and the reaction was stirred for 2h. Add saturated aqueous sodium bicarbonate solution for extraction, take the water phase, add tetrahydrofuran for extraction, take the tetrahydrofuran phase, concentrate under reduced pressure at 40°C, and dry in vacuo to obtain compound Ⅰ as a solid.
[0027] As tested by HPLC, the purity of compound I was 97%.
[0028] The data analysis of compound Ⅰ is shown in Table 1 by MS detection.
[0029] Table 1 MS detection data analysis table of compound Ⅰ
[0030]
[0031] As detected by NMR, the 1H and 13C attribute analysis of compound Ⅰ are ...
Embodiment 2
[0034] Example 2 Preparation of Compound I
[0035] Add 20g of tetrazoleacetic acid into 200ml of dichloromethane, cool down to below -15°C while stirring, add 22ml of triethylamine dropwise, and stir until it dissolves. After 21ml of pivaloyl chloride was added dropwise, 17ml of aminoacetaldehyde dimethyl acetal was added dropwise, and triethylamine was added dropwise to keep the pH at 7.0-8.0, and the reaction was stirred for 3h. Add saturated aqueous sodium bicarbonate solution for extraction, take the water phase, add tetrahydrofuran for extraction, take the tetrahydrofuran phase, concentrate under reduced pressure at 40°C, and dry in vacuo to obtain compound Ⅰ as a solid.
[0036] As tested by HPLC, the purity of compound I was 98%.
Embodiment 3
[0037] Example 3 Preparation of Compound I
[0038] Add 20 g of tetrazolium acetic acid into 240 ml of dichloromethane, cool down to below -15°C while stirring, add 26 ml of triethylamine dropwise, and stir until dissolved. After 23ml of pivaloyl chloride was added dropwise, 15.3ml of aminoacetaldehyde dimethyl acetal was added dropwise, and triethylamine was added dropwise to keep the pH at 7.0-8.0, and the reaction was stirred for 4h. Add saturated aqueous sodium bicarbonate solution for extraction, take the water phase, add tetrahydrofuran for extraction, take the tetrahydrofuran phase, concentrate under reduced pressure at 40°C, and dry in vacuo to obtain compound Ⅰ as a solid.
[0039] As tested by HPLC, the purity of compound I was 96%.
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Abstract
The invention relates to N-(2, 2-dimethoxyethyl)-2-(1H-tetrazol-1-yl) amide and its preparation method and application, belongs to impurity and drugquality research and quality control performed by chemical and pharmaceutical companies, and discloses a structural formula of the N-(2, 2-dimethoxyethyl)-2-(1H-tetrazol-1-yl) amide and its preparation method. The preparation method includes dissolving tetrazoleacetic acid and alkali in methylenechloride for reaction, allowing the resultant to react with pivaloyl chloride to obtain an intermediate A, and allowing the intermediate A to react with aminoacetaldehyde dimethyl acetal to obtain the N-(2, 2-dimethoxyethyl)-2-(1H-tetrazol-1-yl) amide. The N-(2, 2-dimethoxyethyl)-2-(1H-tetrazol-1-yl) amide is mainly used for preparing N-(2, 2-bis-hydroxyethyl)-2-(1H-tetrazol-1-yl) amide, and as an impurity reference for quality research and quality control of bulk drugs and medicaments for cefazolinsodium or pentahydrate cefazolinsodium.
Description
technical field [0001] The invention belongs to the field of chemical pharmacy and relates to N-(2,2-dimethoxyethyl)-2-(1H-tetrazol-1-yl)amide and a preparation method thereof. technical background [0002] Drugimpurity research is an important content in drugquality research, quality control and safety evaluation, and impurity reference substances are the most direct and important research objects in drug impurity research. How to obtain impurity reference substances has become a major issue for most pharmaceuticals. Bottlenecks in quality research, quality control and drug safety evaluation. [0003] In the impurity profile research of cefazolinsodium and cefazolin sodium pentahydrate raw materials and injections, we found that: cefazolin impurity B is N-(2,2-dihydroxyethyl)-2-(1H-tetra Azol-1-yl) amides can be observed by alkaline hydrolysis of cefazolin (HPLC method), but cannot be obtained by conventional methods such as preparation of liquid phase, extraction or pr...
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