N-alkanoyl-N,N′,N′-alkylenediamine trialkanoic acid esters

1. A method of preparing a compound of Formula (I):

wherein:

Z 1 can be present or absent and when present is —[C(R 4 ) 2 ] m —;

m is an integer from 1 to 4;

each X is —CHR 5 —[C(R 6 ) 2 ] n —;

each n is independently an integer from 0 to 4;

R 1 is selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

each R 2 is independently selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

each R 3 and each R 4 are independently selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl, or wherein one R 3 and one R 4 are together alkylene, substituted alkylene, aralkylene, or substituted aralkylene, or wherein two R 4 are together alkylene, substituted alkylene, aralkylene, or substituted aralkylene;

each R 5 is selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl; and

each R 6 is independently selected from the group consisting of H, alkyl, alkoxy, cycloalkyl, aralkyl, aralkoxy, aryloxy, aryl, and substituted aryl; wherein the method comprises:

providing a cyclic amidine compound, wherein the cyclic amidine compound is a cyclic amidine wherein the amidine nitrogen atoms are linked via an alkylene or aralkylene group; and

contacting the cyclic amidine compound with an ester of a haloalkanoic acid in the presence of a base.

2. The method of claim 1 , wherein R 1 is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl, and wherein the cyclic amidine is a compound of Formula (II):

wherein:

Z 2 can be present or absent and when present is —[C(R 9 ) 2 ] m —;

m is an integer from 1 to 4;

R 7 is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl and substituted aryl; and

each R 8 and each R 9 are independently selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl and substituted aryl, or wherein one R 8 and one R 9 together are alkylene, substituted alkylene, aralkylene, or substituted aralkylene, or wherein two R 9 together are alkylene, substituted alkylene, aralkylene, or substituted aralkylene.

3. The method of claim 1 , wherein the cyclic amidine is a 2-substituted imidazoline.

4. The method of claim 3 , wherein the compound of Formula (I) has a structure of Formula (Ia):

wherein:

each X is —CHR 5 —[C(R 6 ) 2 ] n —;

each n is independently an integer from 0 to 4;

R 1 is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

each R 2 is independently selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

R 3 and R 4 are independently selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl, or wherein R 3 and R 4 together are alkylene, substituted alkylene, aralkylene, or substituted aralkylene;

each R 5 is selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl; and

each R 6 is independently selected from the group consisting of H, alkyl, alkoxy, cycloalkyl, aralkyl, aralkoxy, aryloxy, aryl, and substituted aryl.

5. The method of claim 4 , wherein each n is 0.

6. The method of claim 4 , wherein R 1 is alkyl.

7. The method of claim 6 , wherein the alkyl is straight-chain, saturated alkyl.

8. The method of claim 6 , wherein the alkyl is C1-C12 alkyl.

9. The method of claim 8 , wherein the alkyl is C8 alkyl.

10. The method of claim 4 , wherein R 1 has a structure of one of the formulas:

wherein R 1a and R 1b are independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, aralkyl, aryl, and substituted alkyl, and wherein R 1c R 1d and R 1e are independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aralkyl, aryl, and substituted alkyl.

11. The method of claim 4 , wherein each R 2 is C1-C6 alkyl.

12. The method of claim 11 , wherein each R 2 is ethyl.

13. The method of claim 4 , wherein R 3 and R 4 are independently selected from H and alkyl.

14. The method of claim 4 , wherein each R 5 is selected from the group consisting of H and alkyl.

15. The method of claim 4 , wherein the 2-substituted imidazoline is a compound of Formula (IIa):

wherein:

R 7 is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl and substituted aryl; and

R 8 and R 9 are independently selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl and substituted aryl, or wherein R 8 and R 9 together are alkylene, substituted alkylene, aralkylene, or substituted aralkylene.

16. The method of claim 15 , wherein R 7 is saturated alkyl.

17. The method of claim 15 , wherein R 7 is C1-C12 alkyl.

18. The method of claim 15 , wherein one or both of R 8 and R 9 is H.

19. The method of claim 15 , wherein one or both of R 8 and R 9 is alkyl.

20. The method of claim 19 , wherein one or both of R 8 and R 9 is methyl.

21. The method of claim 1 , wherein the ester is the ester of an α-haloacetic acid or a mixture thereof.

22. The method of claim 21 , wherein the ester is ethyl chloroacetate, ethyl bromoacetate, or a mixture thereof.

23. The method of claim 1 , wherein the contacting is performed in an aprotic, non-polar solvent.

24. The method of claim 23 , wherein the aprotic, non-polar solvent is toluene.

25. The method of claim 1 , wherein the base is sodium bicarbonate.

26. A method for preparing a N-acyl-N,N′,N′-alkylenediamine trialkanoic acid or a salt thereof, wherein the method comprises:

providing a cyclic amidine compound, wherein the cyclic amidine compound is a cyclic amidine wherein the amidine nitrogen atoms are linked via an alkylene or aralkylene group;

contacting the cyclic amidine compound with an ester of a haloalkanoic acid in the presence of a first base to provide a compound of Formula (I):

wherein:

Z 1 can be present or absent and when present is —[C(R 4 ) 2 ] m —;

m is an integer from 1 to 4;

each X is —CHR 5 —[C(R 6 ) 2 ] n —;

each n is independently an integer from 0 to 4;

R 1 is selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

each R 2 is independently selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

each R 3 and each R 4 are independently selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl, or wherein one R 3 and one R 4 together alkylene, substituted alkylene, aralkylene, or substituted aralkylene, or wherein two R 4 are together alkylene, substituted alkylene, aralkylene, or substituted aralkylene;

each R 5 is selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl; and

each R 6 is independently selected from the group consisting of H, alkyl, alkoxy, cycloalkyl, aralkyl, aralkoxy, aryloxy, aryl, and substituted aryl; and

contacting the compound of Formula (I) with a second base.

27. The method of claim 26 , wherein the N-acyl-N,N′,N′-alkylenediamine trialkanoic acid or salt thereof is a N-acyl-N,N′,N′-ethylenediamine trialkanoic acid or a salt thereof, and wherein:

providing the cyclic amidine compound comprises providing a 2-substituted imidazoline;

contacting the cyclic amidine compound with the ester of a haloalkanoic acid in the presence of the first base to provide the compound of Formula (I) comprises contacting the 2-substituted imidazoline with the ester of a haloalkanoic acid in the presence of the first base to provide a compound of Formula (I) wherein the compound of Formula (I) is a compound of Formula (Ia):

wherein:

each X is —CHR 5 —[C(R 6 ) 2 ] n —;

each n is independently an integer from 0 to 4;

R 1 is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

each R 2 is independently selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl;

R 3 and R 4 are independently selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl, or wherein R 3 and R 4 together are alkylene, substituted alkylene, aralkylene, or substituted aralkylene;

each R 5 is independently selected from the group consisting of H, alkyl, cycloalkyl, substituted alkyl, aralkyl, aryl, and substituted aryl; and

each R 6 is independently selected from the group consisting of H, alkyl, alkoxy, cycloalkyl, aralkyl, aralkoxy, aryloxy, aryl, and substituted aryl; and

contacting the compound of Formula (I) with the second base comprises contacting the compound of Formula (Ia) with the second base.

28. The method of claim 26 , wherein the second base is an alkali metal hydroxide.

29. The method of claim 26 , wherein contacting the compound of Formula (I) with the second base comprises providing a mixture comprising the compound of Formula (I) and the second base; mixing the mixture for a period of time; and acidifying the mixture with an acid.