Synthesis method of tazobactam diphenylmethyl ester
A technology of zobactam diphenyl methyl ester and a synthesis method is applied in the field of synthesis of tazobactam diphenyl methyl ester, an intermediate of tazobactam, and can solve the problem of high cost of triazole raw materials, no cost advantage, The problem of large amount of triazole, etc., to achieve the effect of short reaction time, simple method and small amount of triazole
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Embodiment 1
[0031] Embodiment 1: Preparation of 1,2,3-triazole sodium salt
[0032] Dissolve 10 g of NaOH (0.25 mol) in 50 ml of purified water, dissolve and cool down to 0-5°C. Put 13.8g (0.2mol) of 1-H-1,2,3-triazole liquid into a three-necked flask, cool down to 5-10°C, add the above-mentioned NaOH solution dropwise, and keep warm for 0.5h after dropping. Slowly add solid NaH at this temperature 2 PO 4 , adjust the pH to 10-11, and keep warm for 1h. After incubation, add 200ml THF to wash and separate layers, then add 200ml THF to wash and separate layers. The water layer was transferred into a one-necked bottle and distilled under reduced pressure to obtain a light yellow oil, which was added with 80ml of absolute ethanol and stirred for 12h to crystallize. Suction filtration yielded 17.3 g of pure white crystalline solid. The sodium ion content of the white solid was detected to be 25.6%, which was basically consistent with the sodium ion content of triazole sodium. The product...
Embodiment 2
[0033] Example 2: Preparation of 2β-[(1,2,3-triazol-1-yl)methyl]penicillanic acid benzhydryl ester
[0034] Dissolve 40.2g (0.1mol) of benzhydryl 2β-chloromethylpenicillanic acid in 500ml dimethyl sulfoxide (DMSO), stir to dissolve, cool down to 0-5°C, and add dropwise a mixture of 1,2 , 3-triazole sodium 11g (0.12mol) and 50ml of water preparation solution. After dropping, keep it warm at 0-5°C for 20 hours. After the reaction was completed, 200ml of water was added, extracted with 400ml of dichloromethane, and the layers were separated. Add 200ml of dichloromethane to the aqueous layer for extraction, and separate the layers. The dichloromethane layers (organic phase) were combined and washed twice with 300 ml of purified water respectively. stand-by.
Embodiment 3
[0035] Example 3: 2β-[(1,2,3-triazol-1-yl)methyl]penicillanic acid diphenylmethyl ester 1,1-dioxide
[0036] Transfer the dichloro feed solution (organic phase) of the above-mentioned 2β-[(1,2,3-triazol-1-yl)methyl]penicillanic acid diphenylmethyl ester into a 1000ml three-necked flask for cooling, and add 200ml glacial acetic acid , 300ml of purified water, continue to cool down to -10-0°C, slowly add 36.6g of potassium permanganate in batches, heat up to 10-15°C for 3 hours after adding, then cool down to below 10°C, add hydrogen peroxide dropwise until the feed liquid is clear After standing still for stratification, the organic phase was washed successively with 200ml of 5% sodium bicarbonate solution and 200ml of water, and the obtained organic phase was distilled under reduced pressure to remove the solvent to obtain an oily substance, and 240ml of acetone was added, and the temperature was raised to 40-50°C to dissolve, and the temperature was lowered. Crystallize at 15...
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