title: A concise synthesis of a β-lactamase inhibitor.
abstract: MK-7655 (1) is a β-lactamase inhibitor in clinical trials as a combination therapy for the treatment of bacterial infection resistant to β-lactam antibiotics. Its unusual structural challenges have inspired a rapid synthesis featuring an iridium-catalyzed N-H insertion and a series of late stage transformations designed around the reactivity of the labile bicyclo[3.2.1]urea at the core of the target.
authors.affiliation: Department of Process Research, Merck and Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. Ian_mangion@merck.com
authors.forename: Ian K
authors.initials: IK
authors.lastname: Mangion
authors.forename: Rebecca T
authors.initials: RT
authors.lastname: Ruck
authors.forename: Nelo
authors.initials: N
authors.lastname: Rivera
authors.forename: Mark A
authors.initials: MA
authors.lastname: Huffman
authors.forename: Michael
authors.initials: M
authors.lastname: Shevlin
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007495:Iridium / Q000737:chemistry; D015394:Molecular Structure; D014508:Urea / Q000737:chemistry; D065093:beta-Lactamase Inhibitors; D047090:beta-Lactams / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D053961:Azabicyclo Compounds; D065093:beta-Lactamase Inhibitors; D047090:beta-Lactams; D007495:Iridium; D014508:Urea; C568736:relebactam