Process for preparing alkyl pyroglutamic acids

Abstract

Disclosed are compounds of formulae: and salts, hydrates, or solvates thereof, where R 1 , R 2 , R 3 , R 5 , and R 6 are defined herein, compositions containing these compounds, methods of preparing these compounds, and methods of using these compounds in a variety of applications, such as a surfactant or additive in personal care products.

1 . A compound of the formula (I): 
       
         
           
           
               
               
           
         
         or acceptable salts, hydrates, or solvates thereof; wherein 
         R 1  is hydrogen, C 1 -C 6  alkyl, C 1 -C 6  hydroxyalkyl, M + , or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped;
 where M +  is a cation forming a salt; 
 
         R 2  and R 3  are independently C 2 -C 24  alkyl, C 2 -C 24  alkenyl, or C 2 -C 24  alkynyl, each optionally substituted with one or more of R 4 ; and 
         wherein R 4  is halogen, —CN, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  haloalkyl, —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl) 2 , C 3 -C 8  cycoalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, —NH 2 , —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl), or —CON(C 1 -C 6  alkyl) 2 ;
 or R 4  is polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped. 
 
       
     
     
         2 . A compound according to  claim 1 , wherein R 1  is hydrogen or M + . 
     
     
         3 . A compound according to  claim 1 , wherein R 1  is a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped. 
     
     
         4 . A compound according to  claim 1 , wherein R 2  is C n  alkyl, and R 3  is C n-2  alkyl, each optionally substituted with one or more of R 4 , and wherein n is 4-12. 
     
     
         5 . A compound according to  claim 4 , wherein n is 5 or 10. 
     
     
         6 . A compound according to  claim 1 , which is: 
       
         
           
           
               
               
           
         
       
     
     
         7 . A composition comprising a compound according to  claim 1 , and at least one additive, excipient or diluent. 
     
     
         8 . A composition comprising at least two compounds selected from the compounds of formula (II): 
       
         
           
           
               
               
           
         
         or acceptable salts, hydrates, or solvates thereof; wherein 
         R 5  is hydrogen, C 1 -C 6  alkyl, C 1 -C 6  hydroxyalkyl, M + , or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped;
 where M +  is a cation forming a salt; 
 
         R 6  is unbranched or branched C 2 -C 24  alkyl, unbranched or branched C 2 -C 24  alkenyl, unbranched or branched C 2 -C 24  alkynyl, C 3 -C 8  cycloalkyl, or C 3 -C 8  cycloalkyl(C 1 -C 6  alkyl), each optionally substituted with one or more of R 7 , and 
         wherein R 7  is halogen, —CN, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, —NH 2 , —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl) 2 , C 3 -C 8  cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, —NH 2 , —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl),
 or —CON(C 1 -C 6  alkyl) 2 , and 
 
       
       of formula (III): 
       
         
           
           
               
               
           
         
         or acceptable salts, hydrates, or solvates thereof; wherein 
         each R 8  is independently hydrogen, C 1 -C 6  alkyl, C 1 -C 6  hydroxyalkyl, M + , or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped;
 where M +  is a cation forming a salt; 
 
         R 9  is unbranched or branched C 2 -C 24  alkyl, unbranched or branched C 2 -C 24  alkenyl, unbranched or branched C 2 -C 24  alkynyl, O 3 —C 8  cycloalkyl, or C 3 -C 8  cycloalkyl(C 1 -C 6  alkyl), each optionally substituted with one or more of R 10 ; and 
         wherein R 10  is halogen, —CN, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, —NH 2 , —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl) 2 , C 3 -C 8  cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, —NH 2 , —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl),
 or —CON(C 1 -C 6  alkyl) 2 . 
 
       
     
     
         9 . A composition according to  claim 8  further comprising at least one additive, excipient or diluent. 
     
     
         10 . A composition according to  claim 8 , comprising at least two compounds of formula (II). 
     
     
         11 . A composition according to  claim 10 , comprising at least two compounds that are: 
       
         
           
           
               
               
           
         
       
     
     
         12 . A composition according to  claim 12 , comprising at least two compounds that are: 
       
         
           
           
               
               
           
         
       
     
     
         13 . A compound according to  claim 1 , for use as a surfactant, surface active additive, or phase transfer catalyst. 
     
     
         14 . A compound according to  claim 1  for use in personal care formulations. 
     
     
         15 . A method of preparing a compound of formula (IV) or a mixture of one or more compounds of formula (IV): 
       
         
           
           
               
               
           
         
         or acceptable salts, hydrates, or solvates thereof; wherein 
         R 11  is hydrogen, C 1 -C 6  alkyl, C 1 -C 6  hydroxyalkyl, M + , or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and can be capped or uncapped;
 where M +  is a cation forming a salt; 
 
         R 12  is unbranched or branched C 3 -C 24  alkyl, unbranched or branched C 3 -C 24  alkenyl, or unbranched or branched C 3 -C 24  alkynyl, each optionally substituted with one or more of R 15 ; and 
         wherein R 15  is halogen, —CN, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, —NH 2 , —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl) 2 , C 3 -C 8  cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, —NH 2 , —NH(C 1 -C 6  alkyl), —N(C 1 -C 6  alkyl) 2 , —OH, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, —CO 2 H, —CO 2 (C 1 -C 6  alkyl), —CON(C 1 -C 6  alkyl),
 or —CON(C 1 -C 6  alkyl) 2 ; 
 
       
       comprising 
       treating a glutamate of formula: 
       
         
           
           
               
               
           
         
         wherein each R 14  is independently selected form hydrogen, M + , C 1 -C 6  alkyl, C 1 -C 6  hydroxyalkyl, —(C 1 -C 6  alkyl-0) 1-4 H, aryl, aryl(C 1 -C 6  alkyl), or polyoxyalkylene unit; 
       
       with an aldehyde of formula: 
       
         
           
           
               
               
           
         
         wherein R 13  is C 1 -C 23  alkyl, C 2 -C 23  alkenyl, or C 2 -C 23  alkynyl, each optionally substituted with one or more of R 15 . 
       
     
     
         16 . A personal care formulation comprising a compound according to  claim 1 . 
     
     
         17 . A personal care formulation comprising a composition according to  claim 7 . 
     
     
         18 . A method for carrying out phase transfer in a reaction system comprising adding to the system a compound according to  claim 1 . 
     
     
         19 . A method for carrying out phase transfer in a reaction system comprising adding to the system a composition according to  claim 7 . 
     
     
         20 . A personal care formulation according to  claim 16 , where the formulation is a shampoo or a body wash formulation.