Although 4-Me 2 NC 5 H 4 N (DMAP) is a standard base for esterification of (2-Me-6-NO 2 -C 6 H 3 CO) 2 O (MNBA), N -methylimidazole (NMI) was examined for the condensation of acids with 1-stearoyl-lysophosphatidylcholine because of the non-tailing nature of NMI on silica gel. Acids tested were EPA, α-linolenic acid, TBS ethers of 18-HEPE and ricinoleic acid, acid-labile epoxy acids, and a phenyldiynyl acid. The condensation proceeded well with these acids, and chromatographic separation of resulting phosphatidylcholines and remaining NMI was easily performed. During the characterization of the products by 13 C NMR spectroscopy, 13 C- 14 N and 13 C- 31 P couplings were observed.
ASJC Scopus subject areas
- Organic Chemistry