L-Serine → 2-Methyl Oleoyl-L-Serine

Participants

Reaction Conditions

Reaction Steps

A solution of L-serine (190 mg, 1.8 mmol) in 20 ml. of 0.1 N sodium carbonate and 0.1 N sodium bicarbonate was added to a solution of N-hydroxysuccinimide ester of 2-methyl oleic acid (204.5 mg, 0.5 mmole) in 20 ml tetrahydrofuran. The reaction mixture was stirred overnight at 35° C., evaporated down to 20 ml, and acidified to pH 1 with 1 N HCl. The product was extracted with methylene chloride (2×20 mL), dried (MgSO4), and the solvent evaporated under reduced pressure. The crude material was chromatographed on silica gel (eluting with chloroform:methanol) to give 86 mg (45%) as a yellowish oil 1H NMR (CDCl3) δ 0.912 (t, 3H), 1.129 (d, 3H), 1.288 (s, 20H), 1.611 (m, 2H), 2.018 (m, 4H), 2.323 (m. 1H), 3.787 (dd, 1H), 3.980 (dd, 1H), 4.503 (t, 1H), 5.353 (m, 2H).

Provenance & Evidence