Synthetic processes and synthetic intermediates

Abstract

The invention provides synthetic intermediates and synthetic processes that are useful for preparing the antibacterial agent TXA709:

1 - 9 . (canceled) 
     
     
         10 . A process for preparing a compound of formula 9: 
       
         
           
           
               
               
           
         
       
       comprising reacting a compound of formula 3: 
       
         
           
           
               
               
           
         
       
       with a compound of formula 8: 
       
         
           
           
               
               
           
         
       
       in acetonitrile to provide the compound of formula 9. 
     
     
         11 . The process of  claim 10 , further comprising preparing the compound of formula 8: 
       
         
           
           
               
               
           
         
       
       by converting a compound of formula 7: 
       
         
           
           
               
               
           
         
       
       to the compound of formula 8. 
     
     
         12 . The process of  claim 11  wherein the compound of formula 7 is converted to the compound of formula 8 by hydrogenation. 
     
     
         13 . The process of  claim 11  wherein the compound of formula 7 is converted to the compound of formula 8 by hydrogenation using palladium on carbon as a catalyst. 
     
     
         14 . The process of  claim 11 , wherein the compound of formula 7 is converted to the compound of formula 8 in the presence of a non-polar solvent. 
     
     
         15 . The process of  claim 11 , wherein the compound of formula 7 is converted to the compound of formula 8 at a temperature in the range from about −78° C. to about 65° C. 
     
     
         16 - 17 . (canceled) 
     
     
         18 . The process of  claim 10 , further comprising converting the compound of formula 9 to TXA709: 
       
         
           
           
               
               
           
         
       
     
     
         19 . The process of  claim 10  further comprising preparing the compound of formula 3 by reacting a compound of formula 2: 
       
         
           
           
               
               
           
         
       
       with a compound of formula: 
       
         
           
           
               
               
           
         
       
     
     
         20 . The process of  claim 19  further comprising preparing the compound of formula 2 by reducing a nitro compound of formula 1: 
       
         
           
           
               
               
           
         
       
       to provide the compound of formula 2. 
     
     
         21 . The process of claim  4  further comprising preparing the compound of formula 1 by reacting a compound of formula: 
       
         
           
           
               
               
           
         
       
       with a compound of formula: 
       
         
           
           
               
               
           
         
       
       to provide the compound of formula 1. 
     
     
         22 . The method of  claim 11  further comprising preparing the compound of formula 7 by converting a compound of formula 6: 
       
         
           
           
               
               
           
         
       
       to the compound of formula 7. 
     
     
         23 . The method of  claim 22  further comprising preparing the compound of formula 6 by carboxylating a compound of formula 5: 
       
         
           
           
               
               
           
         
       
     
     
         24 . The method of claim  8  further comprising preparing the compound of formula 5 by benzylating a phenol of formula 4: 
       
         
           
           
               
               
           
         
       
     
     
         25 . The process of  claim 18 , further comprising preparing a salt of formula 11: 
       
         
           
           
               
               
           
         
       
       by converting TXA709: 
       
         
           
           
               
               
           
         
       
       to the salt of formula 11. 
     
     
         26 . A salt of formula 11, prepared by the process of  claim 25 .