Quaternary bis-ammonium salt diamine fluoride and preparation method thereof
A technology of double quaternary ammonium salt and fluorination, which is applied in the fields of chemical instruments and methods, botanical equipment and methods, and the preparation of organic compounds, etc. It can solve the problem of large amount of single quaternary ammonium salt, increased water absorption of materials, and Gram-negative To solve the problems of poor bacterial effect, etc., to achieve good bactericidal effect, easy source of raw materials, and easy control of the reaction process
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Publication Date
- 2007-03-14
- Estimated Expiration
- Not applicable · inactive patent
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Abstract
Description
technical field
[0001] The invention belongs to the technical field of bisquaternary ammonium salt and its preparation, and in particular relates to a fluorinated bisquaternary ammonium salt diamine and a preparation method thereof. Background technique
[0002] Since Heidelberger (Jacobs WA, Heidelberger M. The quaternary salts of hexamethylene eteramine I. Substituted benzyl halides and the hexamethylene etrammonium salts derived therefrom. J. Biol Chem. 1915; 20: 659-83; Jacobs WA, Heidelberger of M. The bacteria of quaternary prots Hexamethyleneetramine I.the problem of the chemotherapy of experimental bacterial infections.J Exp Med, 1916; 23:563-8) reported in 1915 that quaternary ammonium salts had broad-spectrum bactericidal functions, water-soluble quaternary ammonium salts were used as bactericides in various It has been widely used in the industry. Although quaternary ammonium salts (QAS) have been widely used, studies have also found that some bacteria, especiall...
Examples
Embodiment 1
[0039] The synthetic route is shown in the figure above.
[0040] Step 1): 4.85 grams (14mmol) of α, omega-bishydroxy tert-butoxycarbonate base lysine, 1.58 grams (15mmol) of 2-amino-2-methyl-1,3-propanediol were dissolved in 30ml N , in a mixed solvent of N-dimethylacetamide and 40ml tetrahydrofuran, add 2.94 grams (21.78 mmol) of 1-hydroxybenzotriazole, cool to 0°C with an ice bath, and then add N, N'-bicyclic 3 grams (14 mmol) of hexylcarbodiimide carbon, reacted for 24 hours, removed the precipitate by suction filtration, added 100ml of dilute hydrochloric acid, extracted with ethyl acetate, washed the organic layer with saturated sodium carbonate solution, saturated saline, and water five times, and reduced pressure Concentrate and perform silica gel column chromatography (chloroform:methanol=50:1) to obtain 4.06 g of pure lysine protected with dihydroxy tert-butoxycarbonate groups in the side chain (yield: 67%).
[0041] obtained pure 1 H-NMR (CD3Cl) δppm, 1.27 (m, 2H)...
Embodiment 2
[0051] The synthetic route is shown in the figure above.
[0052] Step 1): 4.85 grams (14 mmol) of α, ω-bishydroxy tert-butoxycarbonate base lysine, 1.58 grams (15 mmol) of 2-amino-2-methyl-1,3-propanediol, dissolved in 30 ml di In the methyl sulfoxide solvent, add 5.73 grams (16.8 mmol) of N-hydroxysuccinimide, cool to 0 ° C with an ice bath, then add 1.85 grams (14.7 mmol), reacted for 36h, removed the precipitate by suction filtration, added 100ml of dilute hydrochloric acid, extracted with ethyl acetate, and the organic layer was washed five times with saturated sodium carbonate solution, saturated brine, and water, concentrated under reduced pressure, and silica gel column chromatography (chloroform: Methanol=50:1), to obtain 4.06 g of pure lysine protected with dihydroxy tert-butoxycarbonate group in the side chain (yield: 67%).
[0053] obtained pure 1 H-NMR (CD3Cl) δppm, 1.27 (m, 2H), 1.43 (m, 23H), 1.80 (m, 2H), 3.12 (m, 2H), 3.70 (m, 3H), 3.89 (m, 2H), 4.01 (s, 2H...