Method for preparing (S)-ornidazole
A technology of levo-ornidazole and nitroimidazole, which is applied in the field of preparation of levo-ornidazole, can solve the problems of low yield, long reaction steps, and high cost of ornidazole optical enantiomers, and achieve high yield, The effect of mild reaction conditions and simple operation
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Embodiment 1
[0015] Embodiment 1: the preparation of L-ornidazole
[0016] Add 20L of ethyl acetate and 2kg of 2-methyl-5-nitroimidazole into a 50L reaction kettle, cool down to -10°C, and slowly add boron trifluoride in ethyl acetate solution (containing boron trifluoride about 1.1kg) (control temperature not exceeding 15°C), after the dropwise addition, slowly add 2.2LS-(+)-epichlorohydrin (control temperature not exceeding 15°C), and react at 10°C for 5 hours after dropping Slowly add the reaction solution into 18kg of ice-water mixture, and stir the reaction for 5 hours at a temperature not exceeding 30°C. Adjust the pH value to about 1.0 with concentrated hydrochloric acid, remove the organic layer, adjust the pH value of the aqueous layer to 7.0 with concentrated ammonia water, stir and crystallize for 24 hour, filter, wash with water, and dry to obtain L-ornidazole 3.21kg. Melting point: 91.5°C-92.5°C[a] D 20 =-68.3 (C=1.0, dichloromethane), purity 99.82%.
Embodiment 2
[0017] Embodiment 2: the preparation of L-ornidazole
[0018] Add 20L of ether and 2kg of 2-methyl-5-nitroimidazole into a 50L reaction kettle, cool down to -15°C, and slowly add a solution of boron trifluoride in ether (containing about 1.1kg of boron trifluoride) ( Control the temperature not to exceed 15°C), after the dropwise addition, slowly add 2.3LS-(+)-epichlorohydrin (control the temperature not to exceed 15°C), and react at 5°C for 5 hours after the dropwise addition, slowly dissolve the reaction solution Add 18kg of ice-water mixture, stir and react at a temperature not exceeding 30°C for 5 hours, adjust the pH value to about 1.5 with concentrated hydrochloric acid, separate the organic layer, adjust the pH value of the aqueous layer to 7.5 with 20% sodium carbonate, stir and crystallize for 24 hours, Filter, wash with water, and dry to obtain 3.13 kg of L-ornidazole. Melting point: 91.0°C-92.5°C[a] D 20 =-68.4 (C=1.0, dichloromethane), purity 99.72%.
Embodiment 3
[0019] Embodiment 3: the preparation of L-ornidazole
[0020] Add 20L of ether and 2kg of 2-methyl-5-nitroimidazole into a 50L reactor, cool down to -15°C, and slowly add boron trifluoride in acetone solution (containing about 1.1 kg of boron trifluoride) ( Control the temperature not to exceed 15°C), after the dropwise addition, slowly add 2.35L S-(+)-epichlorohydrin (control the temperature not to exceed 15°C), and react at 5°C for 4 hours after the dropwise addition, the reaction solution was slowly Slowly add 18kg of ice-water mixture, the temperature does not exceed 30°C and stir for 5 hours, adjust the pH value to about 2 with concentrated hydrochloric acid, separate the organic layer, adjust the pH value of the water layer to 7.0 with 20% sodium hydroxide, stir and crystallize After 18 hours, filter, wash with water, and dry to obtain 3.13 kg of L-ornidazole. 92.0℃-93.0℃[a] D 20 =-68.6 (C=1.0, dichloromethane), purity 99.91%.
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