Synthesis
Under argon protection, 12-bromododecanoic acid (6) (1.0 g, 3.59 mmol) was dissolved in anhydrous methanol (10 mL) containing concentrated sulfuric acid (200 μL) and the reaction was heated to reflux for 15 hours. After completion of the reaction, methanol was removed by distillation under reduced pressure. The residue was diluted with ethyl acetate (100 mL), washed sequentially with saturated sodium bicarbonate solution (3×20 mL) and brine (2×20 mL), and the organic phase was dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to obtain the crude product. Purification by silica gel column chromatography using petroleum ether/ethyl acetate (97.5:2.5) as eluent afforded the target product methyl 12-bromododecanoate (7) (974 mg, 3.32 mmol, 93% yield) as a colorless oil. The product was analyzed by thin-layer chromatography (TLC, Rf 0.45, petroleum ether/ethyl acetate, 9:1), infrared spectroscopy (IR), nuclear magnetic resonance hydrogen spectroscopy (1H NMR), nuclear magnetic resonance carbon spectroscopy (13C NMR) and high-resolution mass spectrometry (HRMS).
References
[1] Journal of Antibiotics, 1995, vol. 48, # 12, p. 1467 - 1480
[2] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1393 - 1400
[3] Analytical Biochemistry, 2014, vol. 456, # 1, p. 70 - 81
[4] Patent: WO2017/49245, 2017, A2. Location in patent: Paragraph 00539-00540
[5] Patent: WO2017/112865, 2017, A1. Location in patent: Paragraph 00618
