Synthetic process for preparing 2-((2-ethoxy-2-oxoethyl)(methyl)amino)-2-oxoethyl 5-tetradecyloxy)furan-2-carboxylate
Disclosed herein are processes for forming 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 mixture of a compound of Formula (II) in an ether solvent; and
combining a compound of Formula (III) with the mixture and a base,
wherein,
R 1 is C 10-20 alkyl;
R 2 is C 1-4 alkyl; and
X is a leaving group.
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 has a boiling point of below 100° C.
5. The process of claim 1 wherein the ether solvent is dialkyl ether.
6. The process of claim 5 wherein the dialkyl ether is methyl t-butyl ether.
7. The process of claim 1 wherein R 1 is —C 14 H 29 and R 2 is ethyl.
8. The process of claim 1 wherein providing the mixture of the compound of Formula (II) comprises coupling a compound of Formula (IV) with X—CH 2 —C(O)Cl in the ether solvent, wherein Formula (IV) has the following structures:
9. The process of claim 8 wherein the coupling is carried out at temperature below 10° C.
10. The process of claim 8 wherein the ether solvent is methyl t-butyl ether.
11. The process of claim 1 wherein the base is an organic base.
12. The process of claim 11 wherein the organic base is triethylamine or trimethylamine.
13. A process for preparing a compound of Formula (I)
comprising:
providing a mixture of a compound of Formula (II) in a solvent having a boiling point of below 100° C.; and
combining a compound of Formula (III) with the mixture and an organic base,
wherein,
R 1 is C 10-20 alkyl;
R 2 is C 1-4 alkyl; and
X is halogen.
14. The process of claim 13 wherein X is Cl.
15. The process of claim 13 wherein the solvent is dialkyl ether.
16. The process of claim 15 wherein the dialkyl ether is methyl t-butyl ether.
17. The process of claim 13 wherein the organic base is triethylamine or trimethylamine.
18. The process of claim 13 wherein R 1 is —C 14 H 29 and R 2 is ethyl.
19. The process of claim 13 wherein providing the mixture of the compound of Formula (II) comprises coupling a compound of Formula (IV) with X—CH 2 —C(O)Cl in the solvent, wherein Formula (IV) has the following structures:
20. The process of claim 19 wherein the coupling is carried out at temperature below 10° C. in the presence of potassium bicarbonate.