1742 br cm-1; 1H NMR 0.86 (br t, 3H), 1.24 (br s, 18H), 1.57 (m, 2H), three.84 (m, 2H), four.16 (t, 2H, J = (CDCl3, 200 MHz) 6.eight Hz), four.25 (m, 1H). 13C NMR (CDCl3, 50 MHz) 14.2, 22.eight, 25.8, 29.1, 29.3, 29.5, 29.7, 29.7, 29.7, 32.1, 65.8, 67.6, 74.five, 173.0. Rf (CHCl3/EtOAc 1:1) 0.36. []D20 -8.four?(c 1.02, CHCl3/MeOH four:1), known compound. four.two.2. 12-[(4-methyl-2-oxo-2H-chromen-7-yl)thio]dodecyl-2,3-dihydroxypropanoate (9b): To a remedy of 7b (0.9304g, 1.84 mmol) in 25 mL 1,4-dioxane was added a answer of HCl (1.six mL of 12 M aq. HCl diluted with 23.5 mL 1,4-dioxane) at area temperature. The reaction was stopped soon after two h. To this mixture 30 mL of benzene were added after which freeze-dried to offer a white residue.201732-49-2 web The strong was dissolved in CHCl3 and purified on a silica gel column loaded with CHCl3 and eluted with CHCl3:EtOAc (5:1). The fractions corresponding to the solution have been combined and evaporated, dissolved in benzene and freeze-dried to provide 9b (0.6612 g, 78 ) as white strong. IR (CHCl3): 3330 br, 1740 br, 1614, 1215 cm-1; 1H NMR (CDCl3, 200 MHz) 1.24 (br s, 16H), 1.62 (m, 4H), two.36 (s, 3H), two.94 (t, 2H, J = 7.two Hz), three.20 (br s, 2H), 3.84 (m, 2H), four.16 (t, 2H, J = 6.8 Hz), four.24 (m, 1H), 6.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTetrahedron. Author manuscript; available in PMC 2015 May well 13.Rosseto and HajduPage(s, 1H), 7.08?.12 (m, 2H), 7.41 (d, 1H, J = 8.eight Hz). 13 C NMR (CDCl3, 50 MHz) 18.4, 25.6, 28.three, 28.five, 28.7, 29.0, 30.0, 29.two, 29.3, 32.0, 64.0, 65.9, 71.6, 113.four, 113.six, 116.7, 122.7, 124.4, 143.7, 152.3, 153.7, 160.7, 172.9. Rf (CHCl3/EtOAc 1:1) 0.23. Anal. Cald for C25H36O6S: C, 64.63; H, 7.81; Discovered: C, 64.84; H, 7.50; MS MH+ C25H36O6SH Calcd: 465.2310, Discovered: 465.2307. []D20 -14.two?(c 0.96, CHCl3) 4.two.3. N-Dodecyl-2,3-dihydroxypropanamide (ten) (i) N-Dodecyl-2,2-dimethyl-1,3-dioxolane-4-carboxamide (eight): To a remedy of 6 (1.1612287-20-3 web 5009 g, 0.PMID:22664133 0103 mmol) in 40 mL of CHCl3 have been added 12-dodecylamine (2.2909 g, 12.four mmol), DMAP (1.3812 g, 11.three mmol) and DCC (two.3315 g, 11.3 mmol) and also the mixture was stirred at area temperature for 16 h. The DCC-urea that formed was filtered as well as the solvent was evaporated. The residue was re-dissolved in CHCl3 and purified on a silica gel column packed with CHCl3 and eluted with CHCl3:EtOAc (10:1). The fractions containing the product had been combined, evaporated, re-dissolved in benzene, and freeze-dried to offer eight (2.9162 g, 90.3 ) as colorless oil that solidified within the freezer. IR (CHCl3): 3345, 1680 br cm-1; 1H NMR (CDCl3, 200 MHz) 0.83 (br t, 3H), 1.21 (br s, 18H), 1.35 (s, 3H), 1.42 (s, 3H), 1.69 (m, 2H), 3.24 (m, 2H), 4.04 (m, 1H), four.23 (br t, 1H), four.43 (br t, 1H), six.58 (m, 1H). 13C NMR (CDCl3, 50 MHz) 14.0, 22.5, 24.5, 24.9, 26.0, 26.7, 29.1, 29.two, 29.4, 29.5, 30.six, 31.eight, 38.eight, 67.6, 74.9, 110.9, 170.9. Rf (CHCl3/EtOAc 5:1) 0.80. []D20 -12.4?(c 1.03, CHCl3), recognized compound.11 (ii) (ten): To a solution of 8 (two.8241 g, 9 mmol) in 25 mL of 1,4-dioxane was added a resolution of HCl (1.6 mL of 12 M aq. HCl diluted in 23.five mL of 1,4-dioxane) at space temperature. Soon after 2.5 h, the mixture became cloudy and formed a white precipitate. To this mixture was added 40 mL benzene, the precipitate was filtered and washed with benzene. The strong was then dispersed in benzene and freeze-dried to give eight (1.5584 g, 5.7 mmol, 63 ) as white powder. The filtrate was collected, freeze-dried, dissolved in CHCl3:EtOAc (1:1) and purified on a silica gel column loaded and eluted with CHCl3:EtOAc (1:1).
