Synthetic process for preparing 2-((2-ethoxy-2-oxoethyl)(methyl)amino)-2-oxoethyl 5-tetradecyloxy)furan-2-carboxylate

1. A process for preparing a compound of Formula (I)

comprising:

providing a compound of Formula (II) combined with a first solvent; and

coupling the compound of Formula (II) with a compound of Formula (III) in a second solvent,

wherein,

R 1 is C 10-20 alkyl;

R 2 is C 1-4 alkyl;

X is a leaving group; and

the first solvent is an ether solvent and is the same as the second solvent.

2. The process of claim 1 wherein X is halogen.

3. The process of claim 2 wherein X is Cl.

4. The process of claim 1 wherein the ether solvent is dialkyl ether.

5. The process of 1 wherein the ether solvent has a boiling point of below 100° C.

6. The process of claim 5 wherein the first solvent and the second solvent are methyl t-butyl ether.

7. The process of claim 1 wherein R 1 is —C 14 H 29 .

8. The process of claim 1 wherein R 2 is ethyl.

9. The process of claim 1 wherein the compound of Formula (I) is 2-((2-ethoxy-2-oxoethyl)(methyl)amino)-2-oxoethyl 5-tetradecyloxy)furan-2-carboxylate.

10. The process of claim 1 wherein providing the compound of Formula (II) combined with the first solvent comprises coupling a compound of Formula (IV) with X—CH 2 —C(O)Cl in the first solvent, wherein Formula (IV) has the following structures:

11. The process of claim 10 wherein the first solvent is an ether solvent having a boiling point of below 100° C.

12. The process of claim 11 wherein the first solvent is methyl t-butyl ether.

13. The process of claim 10 wherein R 2 is ethyl.

14. The process of claim 10 wherein X is halogen.

15. The process of claim 14 wherein X is Cl.

16. The process of claim 1 wherein the coupling of the compound of Formula (II) with the compound of Formula (III) is carried out in the presence of an organic base.

17. The process of claim 16 wherein the organic base is trialkylamine.

18. The process of claim 17 wherein the organic base is triethylamine.