The method for preparing r-lipoic acid choline ester halide
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A lipoic acid choline and halide technology, which is applied in the field of pharmaceutical chemical synthesis, can solve the problems of unspecified preparation conditions and operations, and achieve the effects of safe use, easy-to-obtain reagents, and reasonable technical solutions
Active Publication Date: 2019-02-22
SUZHOU FUSHILAI PHARMA CO LTD
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[0007] But did not give the enlightenment of preparation conditions and operation etc.
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Embodiment 1
[0027] Method A): Add R-lipoic acid (10.0g, 48.5mmol) and toluene (200mL) into a reaction flask, stir to dissolve, add N,N'-dicyclohexylcarbodiimide (12.0g, 58.2mmol) and 4-Dimethylaminopyridine (1.2g, 9.7mmol) was cooled in an ice bath, choline chloride (15.2g, 109.1mmol) was added, and the reaction mixture was reacted at 35°C for 18h. Post-treatment and purification, the crude product was recrystallized with isopropanol to obtain R-lipoic acid choline ester chloride, a light yellow solid (14.8g), with a yield of 93%, and the reaction formula was:
[0028]
Embodiment 2
[0030] Method B): Add R-lipoyl chloride (10.0g, 44.5mmol) and chloroform (200mL) into a reaction flask, stir to dissolve, add N,N-diethylaniline (26.6g, 178.0mmol), cool in an ice bath, Choline chloride (18.6g, 133.5mmol) was added, and the reaction mixture was reacted at 20°C for 12h. Post-treatment and purification, the crude product was recrystallized with isopropanol to obtain R-lipoic acid choline ester chloride, a light yellow solid (12.7g), with a yield of 87%, and the reaction formula was:
[0031]
Embodiment 3
[0033] Method A): Add R-lipoic acid (10.0g, 48.5mmol) and 1,2-dichloroethane (200mL) into the reaction flask, stir to dissolve, add N,N'-carbonyldiimidazole (8.6g, 53.3mmol ) and 2,6-lutidine (0.5g, 4.8mmol), cooled in an ice bath, added choline bromide (26.8g, 145.4mmol), and the reaction mixture was reacted at 20°C for 24h. Post-treatment and purification, the crude product was recrystallized with isopropanol to obtain R-lipoic acid choline ester bromide as a light yellow solid (17.1g), with a yield of 95%. The reaction formula is:
[0034]
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Abstract
The invention provides a method for preparing R-lipoic acid choline ester halide, and belongs to the technical field of chemical synthesis of drugs. The method comprises a method B or a method B, wherein the method A comprises performing an esterification reaction between R-lipoic acid and halogenated choline in a system composed of a dehydrating agent, a catalyst and a solvent to obtain R-lipoic acid choline ester halide I; and the method B comprises performing an esterification reaction between R-sulfenyloctanoylchloride and halogenated choline in a system composed of an acid-binding agent alkali and a solvent to obtain the R-lipoic acid choline ester halide I. The reaction of each step has fewerimpurities, and the operations of after treatment, purification and the like are simplified; the method is safe to use, and suitable for industrial large-scale production; and a green and environmental protection effect is reflected.
Description
technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to a method for preparing R-lipoic acid choline ester halide. Background technique [0002] Lipoic acid (α-Lipoic acid) is a biologically active natural product that was first isolated from pig liver by Reed in 1951. Lipoic acid contains a chiral center. Studies have shown that the two enantiomers of lipoic acid, the R-enantiomer has biological activity, while the S-enantiomer is basically inactive and non-toxic. Lipoic acid has been widely used in the field of clinical medicine in Europe and America, such as liver disease, senile dementia, cataract, heart disease, diabetes, AIDS, psoriasis, eczema, Parkinson's disease, rheumatism, heart disease, neurological disease, subacute necrosis It is known as "universal antioxidant" for the treatment of diseases such as encephalopathy, radiation injury, and heavy metal poisoning. With the in-depth rese...
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