Chemical engineering processes and apparatus for the synthesis of compounds

Abstract

The present invention provides methods for producing cannabinoids and cannabinoid analogs as well as a system for producing these compounds. The inventive method is directed to contacting a compound according to Formula I or Formula II with a cannabinoid synthase. Also described is a system for producing cannabinoids and cannabinoid analogs by contacting a THCA synthase with a cannabinoid precursor and modifying at least one property of the reaction mixture to influence the quantity formed of a first cannabinoid relative to the quantity formed of a second cannabinoid.

1 . A method of producing a compound of Formula II, comprising:
 reacting a compound according to Formula III with a compound according to Formula IV in the presence of a geranyl transferase enzyme:   
       
         
           
           
               
               
           
         
         to produce the compound of Formula II; 
       
       wherein
 R is OH; 
 R 1  is —COOH; 
 R 2  is selected from the group consisting of linear or branched CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 6 H 13 , C 7 H 15  and C 8 H 17 ; 
 R 3  is H; 
 R 5  is 
 
       
         
           
           
               
               
           
         
         wherein R 6  is CH 3 ; and 
       
       wherein the geranyl transferase enzyme is a GPP olivetolate geranyltransferase. 
     
     
         2 . The method of  claim 1 , wherein R 2  is selected from the group consisting of linear CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 6 H 13 , C 7 H 15  and C 8 H 17 . 
     
     
         3 . The method of  claim 2 , wherein R 2  is a linear C 3 H 7  group. 
     
     
         4 . The method of  claim 1 , further comprising contacting the compound of Formula II with a cannabinoid synthase to obtain a cannabinoid or cannabinoid analog; and
 wherein the cannabinoid synthase is selected from the group consisting of a cannabidiolic acid (CBDA) synthase and a tetrahydrocannabinolic acid (THCA) synthase.   
     
     
         5 . The method of  claim 4 , wherein the cannabinoid synthase is CBDA synthase. 
     
     
         6 . The method of  claim 4 , further comprising isolating the cannabinoid or cannabinoid analog. 
     
     
         7 . The method of  claim 4 , further comprising decarboxylating the cannabinoid or cannabinoid analog. 
     
     
         8 . The method of  claim 4 , wherein the cannabinoid or cannabinoid analog is a single enantiomer. 
     
     
         9 . The method of  claim 4 , wherein the enantiomeric purity of the compound of Formula II is at least 95%. 
     
     
         10 . The method of  claim 9 , wherein the enantiomeric purity of the cannabinoid or cannabinoid analog is at least 99%.