L-Serine → N-Oleoyl-L-Serine

Beteiligte Stoffe

Reaktionsschritte

A solution of hydroxysuccinimide ester of oleic acid (395 mg, 1 mmole) in tetrahydrofuran (10 ml) was added to a solution of L-serine (105 mg, 1 mmole) and sodium bicarbonate 84 mg, 1 mmole) in water (10 ml). The reaction mixture was let stirring overnight at room temperature, evaporated down to 10 ml, and acidified to pH 1 with 1 N HCl. The product was extracted with methylene chloride (2×20 mL) and dried (MgSO4) and the solvent evaporated under reduced pressure. The crude material was chromatographed on silica gel (eluting with chloroform:methanol) to give 221.7 mg (60%) as a white powder, m.p. 118 C, NMR (CD3OH, ppm): 5.35-5.32 (m, 2H), 4.57-4.36 (m, 1H), 3.90-3.85 (dd, J=12 Hz, 6 Hz, 1H), 3.82-3.78 (dd, J=12Hz, 6 Hz, 1H), 2.29-2.24 (t, 2H), 2.03-1.98 m, 4H), 1.68-1.58 (m, 2H), 1.32-1.29 (m, 22H), 0.91-0.87 (t, 3H). GC-MS (dTMS): 513, 498, 250, 132 m/z; LC-MS(−p): (M-H)+=368 m/z.

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