171176-56-0

Basic information

• Product Name: Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
• Synonyms: Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS NO: 171176-56-0
• Molecular Weight: 444.413
• Mol File: 171176-56-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate(171176-56-0)
• EPA Substance Registry System: Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate(171176-56-0)

Safety Data

• Hazardous Substances Data: 171176-56-0(Hazardous Substances Data)

Upstream product

• 151860-15-0 (1α,5α,6α)-3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane 
• 151860-16-1 (1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane 
• 100491-29-0 ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 171176-55-9 Ethyl (1α,5α,6α)-7-(6-nitro-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 185693-08-7 (1α,5α,6α)-6-amino-3-azabicyclo[3.1.0]hexane 

Downstream Products

• 146836-84-2 trovafloxacin mesylate 

Relevant articles and documents

Synthesis of trovafloxacin using various (1α,5α,6α)-3-azabicyclo[3.1.0]hexane derivatives

Trovafloxacin, a novel broad spectrum antibacterial, contains the unusual (1α,5α,6α)-3-azabicyclo[3.1.0]hexane ring system. The prototype of the industrial synthesis of this ring system and possible mechanistic pathways to exclusive formation of the exo or 6α-nitro derivative 4 are described, which leads to the key 6a-nitro-3-azabicyclo[3.1.0]hexane intermediate 10. The synthesis of 6a-amino-3-azabicyclo[3.1.0]hexane 16 and useful protected cxo 6-amino derivatives 15 and 17 follows from 10. These can be coupled with the 7-chloronaphthyridone 18 to yield protected trovafloxacin compounds 20-22 in good yield. The ethyl ester of trovafloxacin 21 can also be accessed from the product of coupling 19, derived from 18 and the exo 6-nitro-3-azabicyclo[3.1.0]hexane compound 12. Removal of protecting groups from 20-22 with methanesulfonic acid yields trovafloxacin mesylate from which trovafloxacin zwitterion 1 can be liberated with base treatment. Zwitterion l can also be prepared directly from 16 tosylate salt and naphthyridone-2-carboxylic acid 26. The Royal Society of Chemistry 2000.