1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(3-t-Butoxycarbonylamino-1-pyrrolidinyl)-1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

To a suspension of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (2 g) in anhydrous acetonitrile were added 3-t-butoxycarbonylaminopyrrolidine (1.86 g) and 1,8-diazabicyclo[5,4,0]undec-7-en (DBU, 1.02 g) and then the mixture was refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in chloroform (50 ml). The resulting solution was washed with 10% aqueous citric acid solution (20 ml), and with saturated saline solution successively. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was dissolved in hot methanol (20 ml) and then cooled. The resulting crystals were collected by filtration to give 7-(3-t-butoxycarbonylamino-1-pyrrolidinyl)-1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (2.25 g) as yellowish white prisms, mp 224°-226° C. (decompd.).

1. temperaturethe mixture was refluxed for 3 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. dissolutionthe residue was dissolved in chloroform (50 ml)
4. washThe resulting solution was washed with 10% aqueous citric acid solution (20 ml)
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in hot methanol (20 ml)
8. temperaturecooled
9. filtrationThe resulting crystals were collected by filtration

ORDレコード

ord-fb9bc14485aa423789f207b4804abc8d

出典データセット

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05043450