146836-84-2

Basic information

• Product Name: trovafloxacin
• Synonyms: 1,8-Naphthyridine-3-carboxylic acid, 7-(6-amino-3-azabicyclo(3.1.0)hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-, (1alpha,5alpha,6alpha)-, monomethanesulfonate
• CAS NO: 146836-84-2
• Molecular Formula: C20H15F3N4O3
• Molecular Weight: 416.3533096
• Mol File: 146836-84-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 630.5°Cat760mmHg
• Flash Point: 335.1°C
• Appearance: /
• Density: g/cm³
• Refractive Index: 1.672
• CAS DataBase Reference: trovafloxacin(CAS DataBase Reference)
• NIST Chemistry Reference: trovafloxacin(146836-84-2)
• EPA Substance Registry System: trovafloxacin(146836-84-2)

Safety Data

• Hazardous Substances Data: 146836-84-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16+

Upstream product

• 75-75-2 methanesulfonic acid 
• 210236-57-0 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 185559-52-8 (1α,5α,6α)-3-N-benzyl-6-[t-butoxycarbonylamino]-3-aza-bicyclo[3.1.0]hexane 
• 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 
• 288628-57-9 (1α,5α,6α)-6-Benzylideneamino-3-azabicyclo[3.1.0]hexane 
• 185693-08-7 (1α,5α,6α)-6-amino-3-azabicyclo[3.1.0]hexane 
• 134575-17-0 tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate 
• 151860-17-2 (1α,5α,6α)-3-N-benzyl-6-amino-3-aza-bicyclo[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 
• 134575-66-9 7-([1α,5α,6α]-6-tert-Butoxycarbonylamino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid,ethyl ester 
• 288628-59-1 Ethyl (1α,5α,6α)-7-(6-benzylideneamino-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 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 
• 210165-72-3 7-((1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 

Relevant articles and documents

Process for preparing trovafloxacin acid salts

Trovafloxacin acid salts are prepared via the hydrolysis of imine intermediates using mineral acid including, but not limited to, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, nitric acid, sulfuric acid, phosphoric acid, hydrochloric ac

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.