Method for catalyzing amino protection by imidazole hydrochloride
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An imidazole hydrochloride catalyzed ammonia and amino protection technology, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve problems such as toxicity, corrosion, high cost, etc., and achieve good functional group tolerance , the effect of short response time
Active Publication Date: 2019-07-19
CHONGQING MEDICAL UNIVERSITY
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However, most of these reactions suffer from problems such as high cost, corrosion and toxicity
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Embodiment 1
[0051] Example 1 General Method for Michael Addition to Occur (1a-1t)
[0052] Amine (1 equivalent), imidazole hydrochloride (0.3 equivalent) and N,N-dimethylacetamide 5 mL were added to a 50 mL three-neck round bottle. Warm the resulting solution to 120°C and stir the reaction at this temperature. TLC plate detection, when the reaction is complete, cool to room temperature, add ethyl acetate (30ml), then add activated carbon for decolorization, filter, and wash with saturated brine organic layer. The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was removed under reduced pressure, and purified by silica gel column to obtain the target product.
[0053] General method for deprotection (2a-2f)
[0054] Into a 50 mL three-neck round bottle were added Michael addition product (1 equivalent), imidazole hydrochloride (0.7 amount). The resulting mixture was heated to 150°C and stirred at this temperature for reaction, detected by TLC spot plate, whe...
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Abstract
The invention provides an amino protection method which realizes multi-substituted amino protection by using imidazole hydrochloric acid as an accelerator to push derivatives of primary amine, secondary amine and acrylamide to perform Michael addition at a relatively low temperature, wherein the imidazole hydrochloric acid promotes a carbon-nitrogen bond to crack back to the derivatives of primaryamine and acrylamide at a high temperature. The method provided by the invention is simple and economical, high in practicability, free of any other catalysts or additives, capable of protecting amino to have good functional group tolerance and excellent yield and purity, short in reaction time, free from harsh reaction conditions and suitable for industrial production.
Description
technical field [0001] The present invention relates to the protection of amino groups, in particular to a method of using imidazole hydrochloride to promote the Michael addition of derivatives of primary amines, secondary amines and acrylamide, the addition occurs at a lower temperature, and the carbon-nitrogen bond breaks at a high temperature Going back to the raw materials, methods of forming primary and secondary amines. Background technique [0002] Many drug intermediates or active molecules usually contain amino groups, but the stability of amino groups is poor and the groups are easily oxidized, so amino groups often need to be protected during drug synthesis. Traditionally, amines were reacted with benzyl chloroformate in the presence of inorganic bases (Yang, B.; Shi, L.; Wu, J. et al. Tetrahedron 2013, 69, 3331; Spaulding, A.; Takrouri, K. ; Mahalingam,P., et al.Bioorg Med Chem Lett. 2017,27,5310.), di-tert-butyl dicarbonate (Samadi,S.; Jadidi,K.; Khanmohammadi,...
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