10209-03-7

Upstream product

• 186581-53-3 diazomethane 
• 4888-90-8 phenoxymethylpenicillin sulfoxide 
• 36231-31-9 Dicloxacillin S-sulphoxide 
• 3116-76-5 dicloxacillin 
• 132-98-9 penicillin V potassium 
• 67-56-1 methanol 
• 2315-05-1 methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 

Downstream Products

• 22297-57-0 3-Methyl-2-[3-oxo-4-(2-phenoxy-acetylamino)-3H-isothiazol-2-yl]-but-2-enoic acid methyl ester 
• 61348-77-4 3-Methyl-2-[(2-phenoxymethyl-thiazole-4-carbonyl)-amino]-but-3-enoic acid methyl ester 
• 99346-30-2 (R)-2-[(2R,3R)-2-(4-Methoxy-phenyldisulfanyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester 
• 97748-41-9 (R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-phenyldisulfanyl-azetidin-1-yl]-but-3-enoic acid methyl ester 
• 153785-01-4 (R)-2-[(2R,3R)-2-Chlorosulfinyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester 
• 99346-29-9 (R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-p-tolyldisulfanyl-azetidin-1-yl]-but-3-enoic acid methyl ester 
• 87038-61-7 C₁₉H₂₂N₂O₆S₂ 
• 380413-21-8 2-Allyl-2-((1R,5R)-7-oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid dibenzyl ester 
• 380413-12-7 (2S,6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester 
• 380413-11-6 (2R,6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester 
• 380413-16-1 (6R,7R)-4-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dibenzyl ester 
• 380413-09-2 (4R,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester 
• 380413-13-8 (6R,7R)-4-Methylene-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester 
• 380413-10-5 (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester 

Relevant academic research and scientific papers

Synthesis and decarboxylation of Δ2-cephem-4,4-dicarboxylic acids

Penicillin V was converted in 14 steps into Δ2-cephems having hydrogen at C-3, hydrogen or methyl at C-2, and two methoxycarbonyl, two benzyloxycarbonyl, or one methoxycarbonyl and one benzyloxycarbonyl substituent at C-4. Deprotection of these Δ2-cephem-4,4-dicarboxylic acid esters by alkaline hydrolysis (in the case of methyl esters) or hydrogenolysis (in the case of benzyl esters) led in all cases to rapid decarboxylation of the Δ2-cephem-4,4-dicarboxylic acid or Δ2-cephem-4,4-dicarboxylic acid monoester. With hydrogen at C-2, hydrolysis of the dimethyl ester with 1 equiv of base produced a Δ2-cephem. With 2 equiv of base, and with all compounds having methyl at C-2, hydrolysis or hydrogenolysis afforded 4α-substituted-Δ2-cephems. In contrast, simpler benzyl or methyl acetamidomalonates could be deprotected without difficulty to afford stable malonic acids. Reasons for the differences in ease of decarboxylation were examined using semiempirical (AM1) and ab initio (3-21G) molecular orbital calculations. The decarboxylation barriers of unionized cephem or acetamido malonic acids were found to be high (35-40 kcal mol-1). Although the monoanion of acetamidomalonic acid retained a high barrier, the epimeric monoanions of a Δ2-cephem malonic acid decarboxylated with barriers of only 2 kcal mol-1.

Improved Procedure for Conversion of Penicillin V into Monocyclic β-Lactams

Improved procedures for the preparation of the Kamiya compound (3R,4R)-4-(benzothiazol-2'-yldithio)-3-phenoxyacetamidoazetidin-2-one (6) from penicillin V (1) are described.A novel feature is ozonolysis, near room temperature, in aqueous methanol in the p

Structural and Hydrogen Bonding Studies on β-Lactamase Inhibitor Penicillins by PMR Spectroscopy: Part I - Structures of Cloxacillin and Dicloxacillin Sulphoxides

Structural characterization of cloxacillin and dicloxacillin sulphoxides prepared in our laboratory indicates the S-configuration mainly as revealed by Nuclear Overhauser Enhancement (NOE) measurements, hydrogen bonding and aromatic solvent induced shift studies, etc.An interesting method of characterization of S-sulphoxides is based on the association of dimethyl sulphoxide with cloxacillin and dicloxacillin sulphoxides.