3-Aryl-2-hydroxypropionic acid derivative I

Abstract

A novel 3-aryl-2-hydroxypropionic acid derivative, a process and intermediate for its manufacture, pharmaceutical preparations containing it and the use of the compound in clinical conditions associated with insulin resistance.

1 - 11 . (canceled)  
   
   
       12 . A process to prepare a compound of formula IV  
     
       
         
         
             
             
         
       
     
     wherein Q is hydrogen or R q , wherein R q  is a protective group and A is a chiral auxiliary group, —OH or —OR p  wherein R p  is a protective group comprising asymmetric reduction of a compound of the formula VII  
     
       
         
         
             
             
         
       
     
     wherein A is a chiral auxiliary group, —OH, or —OR p , wherein R p  is as defined above and Q is hydrogen, or R q , wherein R q  is as defined above.  
   
   
       13 . The process according to  claim 12  wherein R q  is benzyl.  
   
   
       14 . The process according to  claim 12  wherein R p  is ethyl.  
   
   
       15 . The process according to  claim 13  wherein R p  is ethyl.  
   
   
       16 . The process according to any one of  claims 12  to  15  wherein the asymmetric reduction is carried out by catalytic hydrogenation in the presence of an appropriate chiral catalyst.  
   
   
       17 . The process according to  claim 16  wherein the chiral catalyst is Rh-BINAP or [Et-DuPHOS-Rh(COD)].  
   
   
       18 . The process according to any one of  claims 12  to  15  wherein the asymmetric reduction is carried out by catalytic hydrogenation with an appropriate catalyst, using the chiral auxiliary group to induce the asymmetry.  
   
   
       19 . The process according to  claim 18  wherein the catalyst is palladium on charcoal.  
   
   
       20 . The process according to any one of  claims 12  to  15  wherein A is a chiral amine.  
   
   
       21 . The process according to  claim 20  wherein the chiral amine is (R)-phenylglycinol.  
   
   
       22 . The process according to any one of  claims 12  to  15  wherein A is a chiral alcohol.  
   
   
       23 . The process according to  claim 22  wherein the chiral alcohol is menthol.  
   
   
       24 . The process according to any one of  claims 12  to  15  wherein A is a chiral oxazolidinone.  
   
   
       25 . The process according to  claim 24  wherein the chiral oxazolidinone is (S)-4-benzyl-2-oxazolidinone.