Oxyalkanoyl clinfloxacin derivatives and their preparation methods and applications
A technology of oxyalkanoyl clinfloxacin and its derivatives, which is applied in the field of drug synthesis
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Embodiment 1
[0026] Embodiment 1, the preparation of intermediate N-chloroacetyl Clinfloxacin (IM1)
[0027]
[0028] Add 1 mmol of clinfloxacin hydrochloride and 2 mL of dichloromethane (DCM) into a 100 mL round bottom flask, cool in an ice bath, stir with a magnetic force, and add NaHCO 3 3.5mmol, after 20min, add 2mL of 2.5mmol of 2-chloroacetyl chloride DCM solution dropwise with a constant pressure dropping funnel. 2 O 15mL and DCM 20mL, adjust pH=2-3 with 2N HCl, separate the layers, extract the aqueous phase with DCM (15mL×2), combine the organic phases, wash with saturated NaCl solution (15mL), anhydrous NaCl 2 SO 4 Dry and rotary evaporate to obtain a crude product, separate and purify by column chromatography to obtain a viscous pure product, add ethyl acetate (EA) 5mL to dissolve, add petroleum ether (PE) 10mL while stirring, a large amount of white solid precipitates, suction filter, dry, 10.370 g of intermediate IM was obtained as a white solid with a yield of 83.6%. Th...
Embodiment 2
[0031] Embodiment 2, the preparation of intermediate N-chloropropionyl Clinfloxacin (IM2)
[0032]
[0033] Add 1mmol of CLX hydrochloride and 2mL of DCM to a 100mL round bottom flask, cool in an ice-salt bath, stir with a magnetic force, and add NaHCO 3 4mmol, after 20min, add 2.5mmol of 3-chloropropionyl chloride 2.5mmol in DCM solution 2mL dropwise with a constant pressure dropping funnel. 2N HCl to adjust pH=2-3, separate the layers, extract the aqueous phase with DCM (20mL×2), combine the organic phases, wash with 0.5N HCl (10mL×3), wash with saturated NaCl solution (20mL×2), wash with water ( 10mL×1), anhydrous Na 2 SO 4 Dry and rotary evaporate to get the crude product, add EA 5mL to dissolve, add PE 10mL under stirring, a large amount of white solid precipitates, suction filter, dry to obtain 0.4g of white solid intermediate IM2, the yield is 81%. The results of other synthesis experiments of IM2 are shown in Table 2.
[0034] Other synthetic experimental resul...
Embodiment 3
[0036] Embodiment 3, the preparation of intermediate N-chlorobutyryl Clinfloxacin (IM3)
[0037]
[0038] Add CLX hydrochloride 10mmol and DCM 25mL into a 100mL round bottom flask, stir at -5°C, add NaHCO after 15min 3 40mmol, after 10min, add dropwise the mixture of 2.8mL of 4-chlorobutyryl chloride and 6mL of DCM with a constant pressure dropping funnel. Stir, adjust pH to about 2 with 2N HCl, separate liquid, collect organic phase, wash with water, anhydrous Na 2 SO 4 Dry and rotary evaporate under reduced pressure to obtain a yellow oil, add EA 20mL, stir, add PE 50mL after 20min, a white solid precipitates, stand still, suction filter, dry, and obtain a yellow-white solid, namely intermediate IM3 4.132g, yield 88.08 %. The results of other synthesis experiments are shown in Table 3.
[0039] Other synthetic experimental results of compound IM3 of table 3
[0040]
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