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A technology of florfenicol and synthetic method, which is applied in the field of veterinary drug preparation, can solve the problems of high cost of hydroxyl activation reagents, and achieve the effects of mature processing technology, low processing difficulty and simple process route
Active Publication Date: 2020-05-15
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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[0008] In addition to the above two commonly used dehydroxyfluorination reagents, the dehydroxyfluorination reaction mediated by nonylfluorobutanesulfonyl chloride / hydrogen fluoride / triethylamine system has also been reported (Tetrahedron Asymmetr.,2011,22,1337- 1341), but this method also faces the problem of high cost of the hydroxyl activation reagent used, thus limiting its application in large-scale production
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Embodiment 1
[0036]
[0037] in N 2 Under gas protection, dissolve compound I (2.05g, 5.8mmol) in 35mL of dichloromethane, add triethylamine (acid-binding agent 1, 1.17g, 2.0equiv), replace sulfuryl fluoride gas, and adjust sulfuryl fluoride The pressure was 0.2 MPa, stirred at room temperature, and detected by TLC until the reaction was completed. Add 10 mL of saturated K to the reaction solution 2 CO 3 The solution was quenched, added dichloromethane (2×60mL) for extraction, combined the organic phases, and washed with saturated K 2 CO 3 Washing (2×60 mL), washing with saturated brine (40 mL), drying over anhydrous sodium sulfate, and column chromatography gave Compound II (1.6320 g, 84%). Compound Characterization: 1 H NMR (500MHz, DMSO-d 6 )δ7.87(d, J=7.1Hz, 1H), 7.61(d, J=7.3Hz, 1H), 7.02(s, 1H), 5.88(d, J=3.5Hz, 1H), 4.86(s, 1H), 4.58(s, 1H), 4.47(t, J=8.8Hz, 1H), 4.40(t, J=7.4Hz, 1H), 3.19(s, 3H); 13 C NMR (126MHz, DMSO-d 6 )δ 162.02, 148.11, 139.35, 127.53, 126.40, 71.5...
Embodiment 2
[0039] The method is the same as in Example 1, except that the sulfuryl fluoride pressure is 0.1 MPa, and the reaction yield is 72%.
Embodiment 3
[0041] The method is the same as in Example 1, except that the acid-binding agent 1 is replaced by NaOH (348 mg, 1.5 equiv), the organic solvent is replaced by 1,4-dioxane, the reaction temperature is raised to 50 ° C, and the reaction yield is 73 %.
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Abstract
The invention discloses a synthesis method of florfenicol, wherein the method comprises the steps: by using thiamphenicol as a raw material, carrying out cyclization, rearrangement, dehydroxyfluorination and hydrolysis under the action of sulfuryl fluoride to obtain florfenicol. According to the method, sulfuryl fluoride is used as a dehydroxylation fluorination reagent to replace an ishikawa's reagent adopted in an original process, a large number of ishikawa's reagent frameworks which are difficult to recycle and reuse are avoided, a byproduct obtained after sulfuryl fluoride reaction is sulfuric acid, and compared with an ishikawa's reagent byproduct, the treatment difficulty is low, and the treatment process is mature; the process route provided by the invention is simple, thiamphenicol is used as a raw material, and florfenicol can be directly prepared at a medium yield through a one-pot synthesis method.
Description
technical field [0001] The invention relates to the field of veterinary drug preparation, in particular to a synthesis method of florfenicol. Background technique [0002] Florfenicol, also known as florfenicol, is a chemically synthesized aminoalcohol antibiotic, which has been widely used in the prevention and treatment of bacterial infections in fish and poultry. The drug is the 3-hydroxyl fluoride of Thiamphenicol, which has stronger antibacterial activity than Thiamphenicol. [0003] [0004] In the preparation process of Florfenicol, the introduction of fluorine atoms is one of the key steps in the synthesis of the drug, and most routes adopt the method of dehydroxyfluorination to introduce fluorine atoms during the synthesis process. For example, in the original research route involved in the Florfenicol patent in 1987, dehydroxyfluorination was carried out on primary alcohols containing oxazoline rings by DAST reagent (diethylaminosulfur trifluoride) (US4361557A)...
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