Method of preparing amino carboxylic acids

Abstract

Novel compounds, N,N′-bis(phosphonomethyl)-N,N′-bis(hydroxycarbonylmethyl)urea and N,N,N′,N′-tetrakis(hydroxycarbonylmethyl)urea, suitable for use in preparing N-acyl aminocarboxylic acids that can be readily converted to N-(phosphonomethyl)glycine are provided. The compounds may be formed by the reaction of bis-(phosophonomethyl)urea or urea respectively with carbon monoxide and formaldehyde in the presence of a carboxymethylation catalyst precursor and solvent.

What is claimed is:  
     
         1 . An acetamide equivalent compound selected from the group consisting of compounds having the formula:  
       
         
           
           
               
               
           
         
       
       wherein R 13  and R 14  are independently hydrogen, hydroxymethyl, alkyl, carboxymethyl, phosphonomethyl, or an ester or salt of carboxymethyl or phosphonomethyl; R 15,  R 16  and R 17  are independently alkyl or —NR 3 R 4 ; and R 3  and R 4  are independently hydrogen, hydrocarbyl, or substituted hydrocarbyl.  
     
     
         2 . The compound of  claim 1  wherein R 13 , R 14  R 15,  R 16  and R 17 are independently methyl, ethyl or isopropyl.  
     
     
         3 . The acetamide equivalent compound of  claim 1 , wherein R 15  and R 16  are methyl.  
     
     
         4 . The acetamide equivalent compound of  claim 1 , wherein the acetamide equivalent compound has the formula:  
       
         
           
           
               
               
           
         
       
     
     
         5 . The acetamide equivalent compound of  claim 4 , wherein R 15  and R 16  are methyl.  
     
     
         6 . The acetamide equivalent compound of  claim 4 , wherein R 15  and R 16  are ethyl.  
     
     
         7 . The acetamide equivalent compound of  claim 4 , wherein R 15 , R 16 , and R 17  are methyl.  
     
     
         8 . The acetamide equivalent compound of  claim 4 , wherein R 15 , R 16 , and R 17  are ethyl.  
     
     
         9 . The acetamide equivalent compound of  claim 1 , wherein the acetamide equivalent compound has the formula:  
       
         
           
           
               
               
           
         
       
     
     
         10 . The acetamide equivalent compound of  claim 9 , wherein R 15  and R 16  are methyl.  
     
     
         11 . The acetamide equivalent compound of  claim 9 , wherein R 13 , R 14 , R 15  and R 16  are methyl.  
     
     
         12 . The acetamide equivalent compound of  claim 9 , wherein R 13 , R 14 , R 15 , and R 16  are ethyl.  
     
     
         13 . The acetamide equivalent compound of  claim 9 , wherein R 13  and R 14  are hydrogen; and R 15  and R 16  are methyl.  
     
     
         14 . The acetamide equivalent compound of  claim 9 , wherein R 13  and R 14  are hydrogen; and R 15  and R 16  are ethyl.  
     
     
         15 . A compound having the formula:  
       
         
           
           
               
               
           
         
         wherein R 1  is hydrogen, hydrocarbyl, substituted hydrocarbyl, —NR 3 R 4 , or —SR 6 ;  
         R 3  and R 4  are independently hydrogen, hydrocarbyl, or substituted hydrocarbyl; and  
         R 6  is hydrogen, hydrocarbyl, substituted hydrocarbyl, or a salt-forming cation.  
       
     
     
         16 . The compound as set forth in  claim 15 , wherein R 1  is methyl.  
     
     
         17 . The compound as set forth in claim  93 , wherein R 1  is —NR 3 R 4 .