| 88.1% |
|
150 g of <strong>[41360-32-1]sulfophenylacetic acid</strong> was dissolved in a mixed solvent of 500 mL of dichloromethane and toluene, and the volume ratioofdichloromethane to toluenewas 1.5:4.0, and the mixture was rapidly stirred, and then 120 mL of triethanolamine was added thereto to clarify the solution.The temperature was lowered to -10 ° C to add70.6 g ofcarbonyl diimidazole, and the reaction was kept at -10 ° C for 1.5 h to prepare a mixed acyl imidazoylating agent solution, which was chilled at -15 ° C for use.Preparation of D-(-)-alpha-sulfacillin sodium: 40 g (0.25 mol) of 6-APA was suspended in amixed solution of300 mL of water-acetone-isopropanol in a volume ratio of 1.2:1:2.The temperature was lowered to -5 ° C, and pH 8 was adjusted with triethanolamine water to completely dissolve 6-APA.Under ice bath, a mixed acyl imidazoylating agent solution was added dropwise to the above solution at a dropping rate of 8percent by volume per minute, and the stirring was continued for 10 minutes while maintaining 10 °C.The reaction solution was washed with diethyl ether (70 mL × 2), n-butanol (100 mL ×3), and the organic phase was combined and washed with 20 mL of saturated aqueous sodium chloride to obtain the extract of the diastereomeric Butanolsolution.Decolorized with charcoal, 0.22um membrane filter, pharmaceutical grades of isopropanol was added a pharmaceutical grade methanol mixed organic solvent having a volumevolume ratio of 2.5: 1.8, after the cold reflux 2.5h, controlling the temperature of 8 , and the solution frozen -15 deg.] C, about 30 min the precipitatedwhite solid was filtered, the filtrate was dried over anhydrous sodium sulfate to give D - (-) - alpha- sulbenicillin alcohol solution, then added with water for injection wasplaced in a 10percent sodium hydroxide solution The pH was adjusted to 6-7, and lyophilized to give 35.2 g of a white solid compound, yield:88.1percent, |
| 84% |
|
(1) Dissolving 216 g (1 mol) of sulfoacetic acid in anhydrous 1000 ml of dichloromethane,After adding 202.4 g (2.2 mol) of propionyl chloride,Cold to 0-5 ° C,449.5 g (4.45 mol) of triethylamine was added dropwise, and after completion, the reaction was carried out at 25 ° C for 3 hours.The reaction solution was transferred to a separatory funnel, washed with water, extracted with dichloromethane, and concentrated to give a mixed acid.(2) Weigh 202.3 g (0.85 mol) of 6-APA and 243.3 g (1.19 mol)N,N-bis(trimethylsilyl)-2,2,2-trifluoroacetamide in the reaction flask,After vacuuming, nitrogen gas was applied, and 1200 ml of ethyl acetate was added as a solvent, and the mixture was heated to about 50 ° C for 2 hours. The reaction was completed, lowered to room temperature, washed with water, extracted with ethyl acetate, and then dried and concentrated.(3) using ethanol as a solvent,Cool down to 0-5 ° C,Slowly adding step (1) to obtain a mixed anhydride and 6-APA protected by step (2),Insulation reaction for 45 minutes,Acidified with hydrochloric acid, raised to 25 ° C,Add sodium isooctanoate and naturally crystallize after stirring.filter. Take the filter cake in the reaction flask,Add 1600ml of ethanol-water (v/v=1/2) mixed solvent,The temperature was raised to reflux, and 75 g of activated carbon was added to stir and decolorize for 20 minutes.The mixture was filtered while hot, and then crystallized to obtain 384.7 g of sulphacillin sodium in a yield of 84percent. |
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