Diisopropylethylamine → HCID 86300945, compound

Participants

Reaction Steps

To a solution of (14Z,17Z)-4-((9Z,12Z)-octadeca-9,12-dienyl)-3-((9Z,12Z)-octadeca-9,12-dienyloxy)tricosa-14,17-diene-1,4-diol (450 mg, 0.52 mmol), 4-(dimethylamino)butanoic acid hydrochloride (105 mg, 0.62 mmol), EDCI hydrochloride (120 mg, 0.62 mmol), DIPEA (225 μL, 1.3 mmol) in anhydrous dichloromethane (10 mL) was added DMAP (5 mg). The solution was stirred at room temperature under nitrogen for 64 hours. Upon completion, the solution was concentrated in vacuo to dryness and purified by column chromatography on silica gel 60 (eluted with 1:1 hexanes/Ethyl acetate) to afford (13Z,16Z)-4-hydroxy-4-((9Z,12Z)-octadeca-9,12-dienyl)-3-((9Z,12Z)-octadeca-9,12-dienyloxy)docosa-13,16-dienyl 4-(dimethylamino)butanoate as a colorless oil (375 mg, 75%). 1H NMR (400 MHz, CDCl3) δ 5.43-5.29 (m, 12H), 4.31-4.11 (m, 2H), 3.60-5.29 (m, 2H), 3.27-3.22 (m, 1H), 2.78 (t, 6H, J=6.4 Hz), 2.39-2.28 (m, 3H), 2.24 (s, 6H), 2.09-2.02 (m, 12H), 1.91-1.72 (m, 4H), 1.61-1.23 (m, 60H), 0.90 (t, 9H, J=7.0 Hz).

Provenance & Evidence