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4-[(4R,5S,6S)-2-Carboxy-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrazolidine-1,2-dicarboxylic acid[ No CAS ]
6-[[(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-(((4-nitrobenzyl)oxy)carbonyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium chloride[ No CAS ]
p-nitrobenzyl (4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-8-ium-6-ylsulfanyl)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate[ No CAS ]
[ 120410-24-4 ]
Yield
Reaction Conditions
Operation in experiment
With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 5 - 10℃;pH 7-8;
Step-II: Preparation of Biapenem To a solution of MOPS buffer and THF, p-Nitrobenzyl (4R,5S,6S)-3-(6,7- dihydro-5H-pyrazolo[l ,2-a][l ,2,4]triazol-8-ium-6-ylsulfanyl)-6-(l -hydroxy ethyl)-4-methyl-7-oxo-l-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (Compound of formula-IV) was added at pH 7-8 and cooled to 5-10 C. The mixture was hydrogenated using palladium on carbon as catalyst. The catalyst was filtered and the filtrate was treated with activated carbon and filtered. The filtrate was extracted with dichloromethane and the layers separated. The aqueous layer was degassed. To the aqueous layer, acetone was added to crystallize Biapenem at 20-25 C. The product was filtered, washed with aqueous acetone and dried under vacuum to get Biapenem (Non-Sterile).
With potassium phosphate; water; at 20℃; for 6.0h;
General procedure: [00163] Lactones derived from <strong>[120410-24-4]biapenem</strong>, doripenem and meropenem were isolated as per the following procedure: (0321) [00164] Carbapenem (4-5 g) was dissolved in 1 mL of 50 mM sodium phosphate, pH 7.5. To this, OXA-48 was added to a final concentration of 20 mM, and the mixture was incubated at room temperature for 5-6 h. The mixture was passed through a 10K MWCO 0.5 mL Amicon centrifugal filter, and the carbapenem-derived lactone was purified from the filtrate by HPLC. The HPLC purification employed a C18 semi-preparative column with mobile phases (A) water with 0.1 % TFA, and (B) acetonitrile with 0.1 % TFA. A solvent gradient as used, from 10 % B to 40 % B over the span of 15 min, and elution was monitored at 230 nm. The desired fractions were combined, frozen on liquid nitrogen, and lyophilized. Purity was confirmed by NMR spectroscopy.