Process for preparing biphenyl compounds

Abstract

A process is provided for preparing a compound having the formula (I): said process being conducted by: a) the addition of an oxygen source into a solution of a compound of formula (II) in a water-miscible solvent, b) the addition of a laccase in the solution obtained in a); and c) the possible recovering of the compound of formula (I) thus obtained.

What is claimed is: 
     
         1 . A process for preparing a compound having the formula (I): 
       
         
           
           
               
               
           
         
         wherein:
 R 1  is H or OH; 
 R 2  is a (C 1 -C 6 )alkoxy group; 
 R 3  is H or forms a C═O group with the carbon atom carrying it; 
 R 4  is R or R′;
 R being chosen from the group consisting of: —CHO, —CN, —COR a , —COOR a , —R a , and (C 2 -C 6 )alkenyl groups, R a  being a (C 1 -C 6 )alkyl group; 
 R′ being a (C 1 -C 6 )alkoxy group; 
 
 
         and wherein, when the bond ‘a’ linking the cores A and B is a single bond, then the compound of formula (I) has the following formula (I-1): 
       
       
         
           
           
               
               
           
         
         and when the bond ‘a’ linking the cores A and B is a double bond, then the compound of formula (I) has the following formula (I-2): 
       
       
         
           
           
               
               
           
         
         said process comprising: 
         a) the addition of an oxygen source into a solution of a compound of formula (II) in a water-miscible solvent, said compound of formula (II) having the following formula: 
       
       
         
           
           
               
               
           
         
         
           wherein R 1 , R 2 , and R 4  are as defined above in formula (I), 
           and R′ 3  is H when R 1  is OH and R′ 3  is OH when R 1  is H, 
         
         said water-miscible solvent being chosen from the group consisting of: dioxane, DMSO, acetone, and mixtures thereof; 
         b) the addition of a laccase in the solution obtained after a); and 
         c) the recovering of the compound of formula (I) thus obtained. 
       
     
     
         2 . The process of  claim 1 , wherein the water-miscible solvent is acetone. 
     
     
         3 . The process of  claim 1 , wherein the laccase is from  Trametes versicolor.    
     
     
         4 . The process of  claim 1 , wherein the amount of laccase for one gram of compound of formula (II) is from 1.5 mg to 75 mg. 
     
     
         5 . The process of  claim 1 , wherein the solution of the compound of formula (II) in a water-miscible solvent is prepared by adding said compound of formula (II) in said water-miscible solvent, and adding a buffer solution. 
     
     
         6 . The process according to  claim 5 , wherein the amount of water-miscible solvent is comprised between 5% and 10% of volume in comparison with the total volume of the mixture formed by said solvent and the buffer solution. 
     
     
         7 . The process of  claim 1 , wherein the addition of an oxygen source according to a) is carried out for a sufficient time to saturate the solution in dissolved oxygen. 
     
     
         8 . The process of  claim 1 , wherein the solution of the compound of formula (II) in the water-miscible solvent used for b) is saturated in oxygen. 
     
     
         9 . The process of  claim 1 , wherein the pH of the solution of the compound of formula (II) in the water-miscible solvent is comprised between 4 and 7. 
     
     
         10 . The process of  claim 1 , wherein step c) is a step of recovering the compound of formula (I) by centrifugation or filtration. 
     
     
         11 . The process of  claim 1 , wherein the amount of laccase for one gram of compound of formula (II) is from 3 mg to 15 mg. 
     
     
         12 . The process of  claim 5 , wherein the buffer solution is a sodium acetate buffer. 
     
     
         13 . The process of  claim 7 , wherein the addition of an oxygen source according to step a) is carried out for 5 minutes.