Practical Synthesis of the New Carbapenem Antibiotic Ertapenem Sodium

• Published in: Journal of organic chemistry Vol. 70; no. 19; pp. 7479 - 7487
• Main Authors: Williams, J. Michael, Brands, Karel M. J, Skerlj, Renato T, Jobson, Ronald B, Marchesini, George, Conrad, Karen M, Pipik, Brenda, Savary, Kimberly A, Tsay, Fuh-Rong, Houghton, Peter G, Sidler, D. Richard, Dolling, Ulf-H, DiMichele, Lisa M, Novak, Thomas J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.09.2005; Amer Chemical Soc
• Subjects: Anti-Bacterial Agents - chemical synthesis; beta-Lactams - chemical synthesis; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; DEHYDROPEPTIDASE-I; ONE-POT SYNTHESIS; AMINO-ACIDS; N-FORMIMIDOYL THIENAMYCIN; NUCLEAR MAGNETIC-RESONANCE; LONG-ACTING CARBAPENEM; CARBAMATE FORMATION; CARBON-DIOXIDE; 6-AMINOPENICILLANIC ACID; AQUEOUS-SOLUTION; Antibiotic; Carbapenem derivatives; Thiol; Hydrogenolysis; Nitrogen heterocycle; Sodium compound; Chemical synthesis; Organic carbamate; Ertapenem; Pyrrolidine derivatives; Organic sulfide

A practical synthesis for the large-scale production of the new carbapenem antibiotic, [4R,5S,6S]-3-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt (ertapenem sodium, 1), has be...