Fingolomide O-acetyl amino alcohol is a structurally related impurity derived from the acetylation of the primary hydroxyl group in the amino alcohol moiety of the parent compound. It retains the 19-carbon sphingosine-like backbone with an N-hydroxyethylamine linkage but features an O-acetyl substitution at the terminal hydroxyl, replacing the native primary alcohol. This modification introduces a branched acetyl ester functionality, distinguishing it from Fingolomide's native hydroxyl. The compound arises as a synthetic byproduct during acetylation processes, where partial esterification occurs prior to final deprotection steps. It serves as a critical HPLC reference standard for quantifying acetylated impurities in Fingolomide bulk drug substance.
On RequestCCCCCCCCC1=CC=C(C=C1)CCC(CO)(COC(=O)C)N
InChI=1S/C21H35NO3/c1-3-4-5-6-7-8-9-19-10-12-20(13-11-19)14-15-21(22,16-23)17-25-18(2)24/h10-13,23H,3-9,14-17,22H2,1-2H3
AAKYGVHJYMMHLU-UHFFFAOYSA-N