31.65, 31.54, 30.02, 29.63, 26.53, 26.02, 20.46, 14.75, 13.30. HRMS: calcd for C46H65N5O9 (MH+) 832.4855, discovered 832.4854. Aplaviroc-urazole (27): To a solution of 8b (20 mg, 0.763 mmol) and 27 (70 mg, 0.0839 (458 mL, 0.0229 mmol, 50 mM answer mmol) in tert-BuOH/H2O (three mL/1 mL) was added THPTA(59) in H2O), Copper sulfate 5 hydrate (114 mL, 0.0229 mmol, 50 mg/mL resolution in H2O) and Sodium ascorbate (91 mL, 0.0229 mmol, 50 mg/mL option in H2O) at area temperature and stirred for 30 min. Then, chloroform was added and washed with sat. NaHCO3 aq. and brine. Combined organic layer was dried more than Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (EtOAc/MeOH = 4/1) to provide 27 (43 mg, 52 ) as thin yellow strong. 1H NMR (400 MHz, MeOD-d4): 7.82-7.80 (m, 3H), 7.45-7.43 (m, 2H), 7.26-7.24 (m, 2H), 7.03-7.01 (m, 4H), 6.97-6.95 (m, 2H), four.74 (m, 2H), 4.48 (m, 2H), four.13 (m, 1H), three.95 (m, 2H), 3.68-3.60 (m, 10H), three.54 (t, J = 4.8 Hz, 2H), 3.46-3.38 (m, 4H), two.97-2.84 (m, 2H), 2.74-2.69 (m, 2H), two.54-2.47 (m, 2H), 2.41-2.27 (m, 2H). 2.20-2.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptBioconjug Chem. Author manuscript; obtainable in PMC 2014 April 17.Ban et al.Page(m, 4H), two.02 (t, J = 2.6, 1H), 1.98-1.89 (2H), 1.73-1.53 (m, 8H), 1.40-1.13 (m, 8H), 0.96-0.85 (t, J = 7.two, 4H). 13C NMR (125 MHz, MeOD-d4): 173.51, 171.84, 168.40, 165.80, 160.35, 158.03, 157.15, 155.25, 154.88, 52.16, 46.76, 132.64, 129.53, 128.05, 123.27, 119.67, 118.08, 115.07, 79.13, 70.53, 70.27, 70.13, 69.54, 69.47, 66.93, 56.87, 49.92, 49.88, 40.1221, 39.96, 39.13, 35.30, 31.49, 26.49, 25.96, 21.46, 20.41, 13.15. HRMS: calcd for C56H75N11O12 (MH+) 1094.5669, discovered 1094.5660. Synthesis of model compounds applied in stability studies–1-(2-Hydroxy-5methylphenyl)-4-phenyl-1,two,4-triazolidine-3,5-dione (29). To a solution of p-cresol (80 mg, 0.740 mmol) in THF (five mL) was added NaH (35.5 mg, 0.885 mmol) at 0 . Soon after 20 min, PTAD (127 mg, 0.725 mmol) was added at 0 and stirred at room temperature for three h.Dasabuvir Technical Information Then, EtOAc and 10 HCl were added.1-Oleoyl lysophosphatidic acid site The organic layer was separated and washed once with brine. The resulting aqueous layer was extracted as soon as with EtOAc. The combined organic layer was dried over MgSO4, and concentrated in vacuo.PMID:24120168 The residue was purified by silica gel chromatography (CHCl3/MeOH) to give 29 (158 mg, 75 ) as a white solid. 1H NMR (600 MHz, DMSO-d6): 9.86 (br, 1H), 7.53-7.49 (m, 4H), 7.43-7.40 (m, 1H), 7.19 (d, J = two.0 Hz, 1H), 7.10 (dd, J = 8.3, two.0 Hz, 1H), six.87 (d, J = 8.three Hz, 1H), 2.24 (s, 3H). 13C NMR (150 MHz, DMSO-d6): 151.98, 151.64, 151.46, 131.86, 130.98, 129.56, 128.80, 127.91, 127.72, 126.03, 122.89, 116.57, 19.67. HRMS: calcd for C15H14N3O3 (MH+) 284.1030, discovered 284.1028. Benzyl-3-(N-phenylsuccinimide)-thioether (30). To a option of N-phenylmaleimide (2 eq., 279 mg, 1.610 mmol) in EtOH (2.85 mL)/pH7.0 HEPES buffer (two.85 mL) was added benzylthiol (1 eq., one hundred uL, 0.805 mmol) in MeCN (2.85 mL) at room temperature. Just after 12 h, EtOAc and H2O were added. The organic layer was separated along with the resulting organic layer was extracted twice with EtOAc. The combined organic layer was dried over Na2SO4, and concentrated in vacuo. The residue was precipitated and washed by Et2O/EtOAc to offer 30 (140 mg, 58 ) as white solids. 1H NMR (400 MHz, CDCl3): 7.51-7.26 (m, 10H), four.29 (d, J = 13.6 Hz, 1H), 3.90 (d, J = 13.6 Hz, 1H), 3.64 (dd, J = three.7, 9.3 Hz, 1H), 3.16 (dd, J = 9.3, 18.9 Hz, 1H), 2.58 (dd, J = 3.