Diphosgene → (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol 8 (0.5 g, 1.1 mmol) in anhydrous diethyl ether (10 mL) was added slowly a solution of diphosgene (0.2 mL, 1.8 mmol) in anhydrous diethyl ether cooled to approximately −15° C. The solution was stirred for 1 hour then N,N,N′-trimethyl-1,3-propanediamine (1.3 mL, 8.7 mmol) was added at −15° C. The solution was warmed to room temperature, stirred for 1 hour, and then filtered to remove the ammonium salts and urea. The diethyl ether filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography (100% ethyl acetate) to afford (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamate 23 as a colorless oil (0.15 g, 23%), 1H NMR (400 MHz, CDCl3) δ 5.41-5.29 (m, 6H), 4.85-4.77 (m, 1H), 3.35-3.21 (m, 2H), 2.93-2.81 (m, 3H), 2.31-2.17 (m, 8H), 2.08-1.92 (m, 12H), 1.75-1.64 (m, 2H), 1.64-1.15 (m, 31H), 0.92-0.85 (m, 9H). Rf 0.45 (10% MeOH—CH2Cl2).

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