Amorphous solid succinylated 3-(fatty acid amido)-2-hydroxy-1- (protected hydroxy)-propane salts and methods of making the same
Aspects of the disclosure includes methods for preparing an amorphous solid composition of a fatty acid metal salt. In practicing the subject methods according to certain embodiments, a succinylated 3-(fatty acid amido)-2-hydroxy-1-(protected hydroxy)-propane organic salt is contacted with a metal base to produce a succinylated 3-(fatty acid amido)-2-hydroxy-1-(protected hydroxy)-propane metal salt; and the succinylated 3-(fatty acid amido)-2-hydroxy-1-(protected hydroxy)-propane metal salt is precipitated in a solvent to produce an amorphous solid succinylated 3-(fatty acid amido)-2-hydroxy-1-(protected hydroxy)-propane metal salt composition. An amorphous solid succinylated 3-(fatty acid amido)-2-hydroxy-1-(protected hydroxy)-propane lithium salt is also provided.
1. An amorphous solid 3-(fatty acid amido)-2-succinyloxy-1-(protected hydroxy)-propane lithium salt, wherein the fatty acid is selected from the group consisting of palmitic acid, stearic acid, oleic acid, linoleic acid, myristoleic acid and batyl fatty acid.
2. The amorphous salt of claim 1 , wherein the fatty acid is palmitic acid.
3. The amorphous salt of claim 1 , wherein the protected hydroxy group comprises a dimethoxy-triphenylmethyl protecting group.
4. The amorphous salt of claim 1 , wherein the 3-(fatty acid amido)-2-succinyloxy-1-(protected hydroxy)-propane lithium salt is a compound of Formula I:
5. The amorphous salt of claim 4 , having an X-ray powder diffraction pattern (XRPD) comprising a peak in 2θ at about 19.5°.
6. The amorphous salt of claim 4 , wherein thermogravimetric analysis (TGA) of the amorphous salt is characterized by a single weight loss step.
7. The amorphous salt of claim 6 , wherein the weight loss step begins at about 225° C.
8. The amorphous salt of claim 4 , wherein the amorphous salt has a TGA thermogram that shows a mass loss of less than 1% of the total mass of the sample upon heating from 30° C. to 300° C.
9. The amorphous salt of claim 4 , having an absorption peak at about 44.9° C. by differential scanning calorimetry (DSC).