Diisopropylethylamine → (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-yl 4-(dimethylamino)butanoate

Participants

Reaction Steps

To a solution of (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol (450 mg, 0.54 mmol), 4-(dimethylamino)butanoic acid hydrochloride (135 mg, 0.8 mmol), EDCI hydrochloride (153 mg, 0.8 mmol), DIPEA (260 μL, 1.6 mmol) in anhydrous dichloromethane (10 mL) was added DMAP (5 mg). The solution was refluxed for 3 hours, cooled to room temperature and concentrated in vacuo to dryness. The reaction mixture was purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 1:1 hexanes/ethyl acetate) to afford (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-yl 4-(dimethylamino)butanoate as a colorless oil (236 mg). 5.43-5.29 (m, 2H), 5.05-4.98 (m, 1H), 3.68-3.64 (m, 1H), 3.52-3.46 (m, 1H), 3.40 (t, 2H, J=6.7 Hz), 2.78 (t, 6H, J=6.4 Hz), 2.46-2.35 (m, 4H), 2.32 (s, 6H), 2.09-2.02 (m, 12H), 1.91-1.81 (m, 2H), 1.70-1.48 (m, 6H), 1.41-1.23 (m, 50H), 0.90 (t, 9H, J=6.7 Hz).

Provenance & Evidence