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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
7-Aminocephalosporanic acid (7-ACS) is an inhibitor of bacterial (S. aureus) β-lactamase.
Synonyms: 7-ACA
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 957-68-6 |
Formula : | C10H12N2O5S |
M.W : | 272.28 |
SMILES Code : | CC(OCC(CS[C@@]([H])(N12)[C@H](N)C2=O)=C1C(O)=O)=O |
Synonyms : |
7-ACA
|
MDL No. : | MFCD00005177 |
InChI Key : | HSHGZXNAXBPPDL-HZGVNTEJSA-N |
Pubchem ID : | 441328 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.1% | With boron trifluoride dimethyl carbonate complex; methanesulfonic acid; at 10 - 12℃; for 0.383333h; | The dried four-necked flask was added with 120 g of dimethyl carbonate, boron trifluoride dimethyl carbonate 56 g, methanesulfonic acid 8 g, quickly cool down to 10 C, adding triazine ring 15g, 7-ACA 25g, maintain 10 ~ 12 C reaction for about 23min, samples were detected by HPLC (High Performance Liquid Chromatography). The 7-ACA residue was less than 1%. To the four-necked flask by adding cold water 240g, solution clarification, adding EDTA-2Na 0.25g, Sodium dithionite 1.0g holding temperature below 13 C, dropping diluted ammonia (1: 1) to adjust pH = 2.3 to 2.6, pPrecipitation of white solid, dropwise 5 ~ 10 C crystal growing 1h, filter, the filter cake was washed twice with 120 g of water, filter, wash the filter cake with 50 g of ethanol once, filtration, vacuum drying at 45 C for 8h a solid 32.5g, molar yield 95.1%, purity 99.40%. |
90% | With boron trifluoride dimethyl carbonate complex; edetate disodium; at 30℃; for 0.833333h; | In 1000ml three mouth Bottle in order to join:Dimethyl carbonate (200 ml),7-ACA (35 g, 128.5 mmol),TauTauZeta (20 · 5g, 128 · 8mmol),EDTANa2 (0.4 g, 1.2 mmol)And boron trifluoride-dimethyl carbonate solution (188 ml, 493.1 mmol)(Mass percentage content 20%),The reaction was stirred for 50 minutes at a temperature of 30 C.The temperature of the reaction was reduced to T <15 C,The reaction was terminated by addition of an aqueous solution of sodium hydrogensulfite (250 ml of water +3.5 g of NaHS03)Followed by dropwise addition of 5% aqueous ammonia seed crystal to the system turbidity, slow stirring culture 40min.Then, the pH value of the system was adjusted to 3.8-4.0 by adding 5% aqueous ammonia, and the crystal was slowly incubated for 30 min and the temperature was controlled at 6-7 C.40ml acetonitrile + 40ml washing, two wash with 90ml acetone wash, dry, vacuum dried at 50 C 2h products 42g, molar yield 90%, HPLC purity 99. 2% |
85.71% | With boron trifluoride; In acetonitrile; at 10 - 30℃; for 0.5h; | In a three-necked flask, 100 mL of acetonitrile was added,7-ACA40g (147 mmol),40.4 g (254 mmol) of TTA,Stirring down to 10 C below,150 mL of boron trifluoride-acetonitrile solution [w / w = 18%] was added,The temperature was raised to 30 C and the reaction was carried out for 30 min.Add purified water 300mL in 15min,Heating to 10 ~ 20 reaction 2h,Adding the ammonia water to adjust the reaction liquid to pH 1.6-2.0,The temperature was lowered to 10 C. Filtration, filter cake with acetonitrile - water,Washed with water and dried to obtain 48 mg of 7-ACT in a yield of 85.71%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.5% | 15.9 g of compound I (0.1 mol, M.W. 159) and 28.49 g of compound II (0.11 mol, M.W. 259) were addedInto a reaction flask containing 3.18 g of dimethyl carbonate, stirred at 35 C for 1 hour, followed by the addition of 38.5 g of compound III(0.11 mol, M.W. 350), 3.18 g of PEG-800 was added with stirring, and after stirring for 10 minutes, 0.975 g of triethylamine was added,10 stirring reaction 4 hours, and then dropping 5w.t.% sodium hydroxide solution to pH = 7, by adding excessive acetone, precipitation of white knotCrystal, vacuum drying at 65 C to obtain 65.8 g of compound V (M.W.661), the yield of 99.5%, 99.99% purity, total miscellaneousLess than 0.01%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sulfuric acid; for 0.0666667h;Microwave irradiation; | The method for synthesizing cefpirome sulfuric acid by microwave method according to the present invention,Comprising the steps of:(1) 7-aminocephalosporanic acid (2.72 g, 7-ACA, Compound I, MW272, 0.01 mol) and AE-activity(AEMA, Compound VII, MW 350, 0.011 mol) was mixed and homogeneously ground.(Compound IV, MW 119, 0.011 mol) and concentrated sulfuric acid (10.88 g, 98% by weight) were added to the solution, followed by the addition of 2,30 g of 2,3-cyclopentenopyridine.(2) 300W microwave reaction for 1 minute,450W microwave reaction for 1 minute,750W microwave reaction for 2 minutes;(3) After completion of the reaction,The reaction residue was added to 29.92 g of deionized water,Mixing and filtering,Take filtrate,The solvent was removed,A white solid,50 & lt; 0 & gt; C for 4 hours under vacuum,That is to get the cefpirome sulfuric acid 5.09g (MW514),Yield 99.0%Purity 99.9% or more. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With aluminum (III) chloride; boron trifluoride; carbonic acid dimethyl ester; at 5 - 30℃; for 1h; | Step 1), add 272 g (1.0 mol) of 7-ACA, 1090 ml of dimethyl carbonate, 175 g (1.10 mol) of TTZ to the reaction flask, turn on the stirring, and lower the temperature of the reaction system to 5 C to 10 C. 9.4g of AlCl3-BF3-dimethyl carbonate solution [(wBF3) = 18%] (wherein, AlCl3 0.66g (0.005mol), BF3 1.7g (0.025mol)), after the dropwise addition is completed, the temperature is raised to 20-30 C Incubate for 1 h, add 1500 ml of purified water, add 135 mL of 2% sodium dithionite solution, stir for 1 h, adjust the pH to 2.5 with ammonia, cool to 10 C, suction filter, filter cake with acetonitrile / purified water = 1: 3 The mixed solution was rinsed twice with 100 ml and dried to obtain 347.9 g of 7-ACT, yield: 92%, purity 98.2%. |
90% | With aluminum (III) chloride; boron trifluoride; carbonic acid dimethyl ester; at 5 - 30℃; for 1h; | Step 1), 7-ACA 100g (0.367mol), dimethyl carbonate 400ml, TTZ 64g (0.402mol) are added to the reaction flask, the stirring is started, the reaction system is cooled to 5 C to 10 C, and added dropwise to the reaction system 14.5g AlCl3-BF3-dimethyl carbonate solution [(wBF3) = 18%] (Among them, 1.0g (0.0075mol) of AlCl3, 2.6g (0.038mol) of BF3), after the dropwise addition was completed, the temperature was raised to 20 to 30 C. Incubate for 1h, add 750ml of purified water, dropwise add 50mL of 2% sodium dithionite solution, stir for 1h, adjust the pH to 3 4 with ammonia water, lower the temperature to 10 15 , suction filter, filter cake with acetonitrile / purified water = The mixed solution of 1: 3 was rinsed twice in 100 ml, and dried to obtain 125 g of 7-ACT, with a yield of 90% and a purity of 97.8%. |
Tags: 7-Aminocephalosporanic acid | Aliphatic Cyclic Hydrocarbons | Ketones | Antibacterial | Bile Acid | Steroids | Anti-Infection | Organic Building Blocks | 957-68-6
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