49841-95-4

Upstream product

• 3511-16-8 6-epi-hetacillin 
• 551-16-6 6-Aminopenicillanic Acid 
• 6591-61-3 D-(-)-α-aminophenylacetic acid methyl ester 
• 18715-92-9 6α-((R)-2,2-dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-penicillanic acid 
• 65587-54-4 2',2'-Dibrompropoxycarbonyl-ampicillin-ONa 
• 40439-01-8 hetacillin 

Downstream Products

• 94595-14-9 2-(3,6-dioxo-5-phenylpiperazine-2-yl)-5,5-dimethylthiazolidine-4-carboxylic acid 
• 82922-25-6 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[2-phenyl-2-(2-phenyl-isoureido)-acetylamino]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 82922-24-5 C₃₀H₂₈N₅O₆S^(1-)*Na⁽¹⁺⁾ 
• 51727-23-2 p-bromophenacyl-6-β-<(aminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 82922-26-7 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[2-phenyl-2-(2-o-tolyl-isoureido)-acetylamino]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 82934-39-2 C₃₂H₃₂N₅O₆S^(1-)*Na⁽¹⁺⁾ 
• 96661-43-7 p-bromophenacyl-6-β-<(4-methyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 96661-44-8 p-bromophenacyl-6-β-<(4-n-butyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 96661-42-6 p-bromophenacyl-6-β-<(4-phenyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 96661-46-0 6-β-<(4-methyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid potassium salt 
• 96661-47-1 6-β-<(4-n-butyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid potassium salt 
• 96661-45-9 6-β-<(4-phenyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid potassium salt 
• 22888-48-8 6β-((R)-2-benzylamino-2-phenyl-acetylamino)-penicillanic acid benzyl ester 
• 145236-53-9 (5R,6R)-3,3-Dimethyl-7-oxo-6-(3-oxo-4-phenyl-3H-[1,2,5]thiadiazol-2-yl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 

Relevant academic research and scientific papers

Chemical reactivity of penicillins and cephalosporins. Intramolecular involvement of the acyl-amido side chain

The rate of degradation of 6-epi-ampicillin in acidic, neutral, and alkaline aqueous solutions was followed at 35 °C and an ionic strength of 0.5 mol dm-3 (KCl) by high-performance liquid chromatography (HPLC) and spectrophotometric assays. Pseudo-first-order rate constants were determined in a variety of buffer solutions, and the overall pH-rate profile was obtained by extrapolation to zero buffer concentration. The hydrolysis of 6- epi-ampicillin is subject to acid and hydroxide-ion catalysis and, for a penicillin, an unusual pH-independent reaction. Intramolecular general base- catalyzed hydrolysis by the side chain amido group is proposed to explain the enhanced rate of neutral hydrolysis of 6-epi-ampicillin and cephalosporins. The β-lactam of 6-epi-ampicillin also undergoes intramolecular aminolysis by nucleophilic attack of the 6-α side chain amino group to give a stable piperazine-2,5-dione derivative. The low effective molarity for intramolecular aminolysis of only 40 M is partly attributed to the unfavorable trans to cis isomerization about the 6-amide side chain required for ring closure. Theoretical calculations show that the intramolecular aminolysis of 6-epi-ampicillin nucleophilic attack occurs from the α-face of the β-lactam ring with an activation energy of 14.4 kcal/mol.

Extremely Selective and Mild Cleavage of β-Haloalkyl Groups by Cobalt(I)phthalocyanine Anion in Semisyntheses of β-Lactam Antibiotics

Cleavage of β-haloalkyl groups can be performed extremely selectively by cobalt(I)phthalocyanine anion under very mild conditions, qualifying it best in the chemistry of highly sensitive β-lactam antibiotics.This is demonstrated in penicillin and cephalosporin semisyntheses.