7-((aminophenylacetyl)amino)-3-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicaci
(6R,7S)-7-{[(2R)-2-Ammonio-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, monohydrate
CAS: 121961-22-6
Molecular Formula: C16H16ClN3O4.H2O
7-((aminophenylacetyl)amino)-3-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicaci - Names and Identifiers
7-((aminophenylacetyl)amino)-3-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicaci - Physico-chemical Properties
| Molecular Formula | C16H16ClN3O4.H2O |
| Molar Mass | 367.787 |
| Melting Point | 205-215° (dec) (Matsukuma) |
| Specific Rotation(α) | D21 +34.0° (c = 0.35 in water) |
| Appearance | Off-white solid |
| Storage Condition | 2-8°C，干燥，密闭 |
| Physical and Chemical Properties | Melting point 205~215 ℃ (decomposition). [α]D21 34.0 °(C = 0.35, water). |
| In vitro study | Loracarbef hydrate demonstrates excellent activity against isolates of Escherichia coli and Klebsiella , Proteus and Salmonella species. |
7-((aminophenylacetyl)amino)-3-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicaci - Risk and Safety
| HS Code | 2941906000 |
7-((aminophenylacetyl)amino)-3-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicaci - Reference Information
| biological activity | Loracarbef hydrate is a cephalosporin antibiotic, a synthetic, second-generation carbenicillin beta-lactam antibiotics with oral activity. |
| Use | its antibacterial activity is similar to that of cefaclor and cefuroxime axetil, and it is used for Pneumonia, pharyngitis, chronic bronchitis, mild to moderate acute bronchitis secondary bacterial infection, tonsillitis. |
| production method | Method 1:528mg of compound (I) is dissolved in 15ml of anhydrous benzene, 0.2rnl of thiophenol and 0.2ml of piperidine are added, stir at room temperature for 2H. It was washed with 10% aqueous citric acid solution and saturated brine, dried and concentrated under reduced pressure. The oily residue was subjected to silica gel column chromatography eluting with hexane-ethyl acetate (4:1) to give 96.3% mg of compound (II) in 77.5 yield, melting point -78 °c. m-CPBA mg of compound (II) was dissolved in 50ml of distilled chloroform, and MG of M-chloroperbenzoic acid (m-perbenzoic acid) was added under cooling in an ice bath. After stirring at 0 °c for 30min, the reaction solution was washed with saturated sodium bicarbonate solution and saturated brine, dried and concentrated to give 500mg of compound (III), yield 99.9%, melting point 95.5~96.5 °c. 109mg of compound (III) and 23.5mg of calcium oxide were suspended in 1ml of dichloromethane and 27 μl of sulfuryl chloride was added at 0 °c. And stirred at 0 °c for 1H. The reaction solution was washed with 10% citric acid solution, saturated sodium bicarbonate and saturated brine successively, dried and concentrated. The residue was subjected to silica gel column chromatography eluting with hexane-ethyl acetate (5:1) to give 56.1% of compound (IV) as an oil. 1.3g of compound (IV) was dissolved in 100ml of carbon tetrachloride and refluxed for 6H. After cooling, the reaction solution was concentrated. The residue was subjected to silica gel column chromatography, eluting with n-hexane-ethyl acetate (5:1) to obtain 65.2% mg of compound (V), yield 96.0, melting point -1~97.0. 10% mg of compound (V) and 70mg of 1.2 palladium-carbon catalyst were suspended in mL of ethanol and ML of 1mol/L hydrochloric acid, hydrogenated at room temperature and atmospheric pressure for 3H, and the catalyst was filtered off, and washed with a small amount of ethanol. The filtrate and washings were combined and concentrated. The remaining solid was dissolved in water and washed with ether. The aqueous layer was adjusted to pH 8 with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated to give compound (VI) in the form of 218mg colorless powder in a yield of 68.4%. 102mg of compound (VI) and 1ml of trifluoroacetic acid were reacted at room temperature for 30min. After concentration, the residue was impregnated with diethyl ether to give 75.5% mg of compound (VII) as a yellow powder. A porous ceramic column of about 1mm diameter was treated with γ-aminopropyltriethoxysilane and then treated with glutamine. The crude enzyme (extract of Kluyvera tyrophila KY-7844) was reacted with the porous ceramic treated as described above to obtain an Immobilized enzyme. 9.73g of compound (VII) was dissolved in 580ml of phosphate buffer (Ph = 6.75), and 51g of methyl phenylglycine was added. The mixture was passed through the column containing Immobilized enzyme (185 ml) prepared above, and the internal temperature of the column was maintained at 20 ° C. For 3 cycles for about 8.5 hours. 6.15G of chlorocarbocephalosporin was obtained with a yield of 78.2% and a melting point of 205-215 ℃ (decomposition). Method 2:9.20G of compound (VIII) was dissolved in 100ml of chloroform, 2.83ml of thiophenol and 0.5ml of piperazine were added, and the mixture was stirred for 3 hours. It was concentrated and the residue was subjected to silica gel column chromatography, eluting with n-hexane-ethyl acetate (2:1). 9.26G of colorless crystals of the compound (IX) were obtained in a yield of 77.5%. 4.78G of the compound (IX) was dissolved in 10% of chloroform, and 2.37G of chloroperoxybenzoic acid was added at 0 ° C. After stirring for 30min, 1 ml of sodium thiosulfate solution was further added. The organic layer was separated, washed with saturated sodium bicarbonate and saturated brine, dried and concentrated. The remaining white solid was dissolved in 50ml of dichloromethane, 1.45ml of sulfuryl chloride was added under ice-cooling, and the mixture was stirred at 0 °c for 1H. After dilution with 50ml of dichloromethane, it was washed with 10% citric acid solution, sodium bicarbonate solution and saturated brine successively, dried and concentrated. The obtained colorless powder was dissolved in 80ml of toluene, refluxed for 2H, and concentrated. The residue was chromatographed on silica gel eluting with n-hexane-ethyl acetate (1:1) to give 87% G of colorless crystals of compound (X) with a melting point of 177.6 °c. 1.7g of compound (X) and 8ml of trifluoroacetic acid were stirred at 0 °c for 1H. After concentration under reduced pressure, a brown oil was obtained. After impregnation with diethyl ether, 1.1g of compound (y) was obtained in a yield of 71.8%. 10.96G compound (↑) After being dissolved in 1.85 of water and treated with 0.2 times of hydrazine hydrate, the Ph was adjusted to 7.5 to 7.7 with mol/L of sodium hydroxide. After stirring at 5 °c for 3H, the temperature was raised to 35 °c, acidified with 1mol/L hydrochloric acid to Ph = 0.8, and left for 4H. The precipitate was removed by filtration and the filtrate was concentrated to 93mL and left overnight at room temperature. The precipitated precipitate was collected by filtration and dried to give 5.54G of a crude compound (VII) with a purity of 83.5% and a yield of 70.6%. After purification by chromatography, crystals of colorless compound (VII) were obtained. Compound (VII) chlorocarbocephalosporins can be obtained according to Method 1. |
Last Update：2024-04-10 22:29:15
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View History
7-((aminophenylacetyl)amino)-3-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicaci
1-Boc-3-CyanoMethylpiperidine
2-Oxepanone, polymer with 2-aminoethanol, 5-amino-1,3,3-trimethylcyclohexanemethanamine, 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, 1,1'-methylenebis[4-isocyanatocyclohexane] and 2,2'-oxybis[ethanol]
1-[4-(but-3-en-1-yloxy)-3-fluorophenyl]ethan-1-one
2-Cyclopentene-1-methanamine,2-ethoxy-N-methyl-1-(2-methyl-2-propenyl)-(9CI)
Borane - 5-Ethyl-2-Methylpyridine CoMplex
Propanoic acid, 3-(methylsulfonyl)-, 2,5-dioxo-1-pyrrolidinyl ester
2-(N,N-DIMETHYLSULFAMOYL)PHENYLBORONIC ACID
Acetamide, 2,2,2-trifluoro-N-[4-methyl-3-(trifluoromethyl)phenyl]-
4-Iodo-2-(methylsulphanyl)pyrimidine
1-Boc-3-CyanoMethylpiperidine
2-Oxepanone, polymer with 2-aminoethanol, 5-amino-1,3,3-trimethylcyclohexanemethanamine, 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, 1,1'-methylenebis[4-isocyanatocyclohexane] and 2,2'-oxybis[ethanol]
1-[4-(but-3-en-1-yloxy)-3-fluorophenyl]ethan-1-one
2-Cyclopentene-1-methanamine,2-ethoxy-N-methyl-1-(2-methyl-2-propenyl)-(9CI)
Borane - 5-Ethyl-2-Methylpyridine CoMplex
Propanoic acid, 3-(methylsulfonyl)-, 2,5-dioxo-1-pyrrolidinyl ester
2-(N,N-DIMETHYLSULFAMOYL)PHENYLBORONIC ACID
Acetamide, 2,2,2-trifluoro-N-[4-methyl-3-(trifluoromethyl)phenyl]-
4-Iodo-2-(methylsulphanyl)pyrimidine