Triethylamine → HCID 131730101, compound

Participants

Reaction Steps

Another batch of IX was prepared as follows: to a solution of VIII (1.60 g, 1.78 mmol), Et3N (0.50 mL, 3.56 mmol) and DMAP (22 mg, 0.178 mmol), in CH2Cl2 (12 mL) was added dropwise myristoyl chloride (0.53 mL, 1.96 mmol) at 0° C. The reaction mixture was allowed to warm up slowly to room temperature. After stirring 24 h at room temperature, the reaction mixture was diluted with CH2Cl2 (50 mL), washed sequentially with 5% aqueous sodium bicarbonate (15 mL), water (15 mL), and saturated aqueous NaCl (15 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 0.2% MeOH in CHCl3) furnished 17 (1.60 g, 81%) as oily liquid. NMR spectra coordinates are as follows: 1H NMR (CDCl3): δ 7.34-7.05 (m, 35H), 5.05-4.96 (m, 1H), 3.53-3.42 (m, 4H), 3.08 (dd, J=10.0, 3.2 Hz, 1H), 2.99 (dd, J=10.0, 6.0 Hz, 1H), 2.68-2.54 (m, 6H), 2.25 (t, J=8.0 Hz, 2H), 1.64-1.55 (m, 2H), 1.35-1.14 (m, 20H), 0.98 (s, 118H), 0.88 (t, J=6.8 Hz, 3H).

Provenance & Evidence