Ed (higher vacuum), dissolved in CH2Cl2:CH3OH (90:10 by vol), and eluted by way of a column of silica applying CH2Cl2:CH3OH (93:7 by vol). A deep red compound was collected. The solvent was removed providing pure three. Yield: 10 mg (50 ); m.p.: 276 ; IR (KBr): V = 3444, 2970, 1669, 1636, 1386, 1265, 1168, 981, 758, 669 cm-1; 1H NMR ((CD3)2SO): = 1.07 (6H, t, J = 7.three Hz), 1.77 (6H, s), 2.04 (6H, s), 2.33 (4H, t, J = 7.3 Hz), two.51 (4H, q, J = 7.three Hz), two.76 (3H, t, J = 7.3 Hz), 5.94 (2H, s), six.88 (2H, s), ten.17 (2N-H, bs), ten.28 (2N-H, bs), 12.20 (2COOH, vbs) ppm; 13C NMR ((CD3)2SO): = 8.61, 9.68, 15.33, 17.63, 20.00, 35.63, 97.23, 113.41, 123.57, 124.04, 124.17, 125.79, 129.86, 132.54, 147.55, 172.56, 174.40 ppm; UV-Vis information in Table five.Monatsh Chem. Author manuscript; accessible in PMC 2015 June 01.Pfeiffer et al.Page(4Z,15Z)-2,2 -(1,2-Ethenediyl)bis[5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2ylidine)methyl]-4-methyl-1H-pyrrole-3-butanoic acid] dimethyl ester (4eC38H48N4O6)NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptHomorubin dimethyl ester 2e (40 mg, 0.061 mmol) was treated as in the synthesis of 3e above to offer crude 4e. The crude solution was purified using radial chromatography working with CH2Cl2:CH3OH (99:1 by vol). Yield: 28 mg (72 ); m.p.: 264 ; 1H NMR: = 1.ten (6H, t, J = 7.2 Hz), 1.70 (4H, quint, J = 7.5 Hz), 1.90 (6H, s), 2.05 (6H, s), two.30 (4H, t, J = 7.5 Hz), 2.50 4H, q), two.60 (4H, t, J = 7.5 Hz), three.55 (6H, s), five.95 (2H, s), 6.90 (2H, s), 10.20 (2H, brs), ten.30 (2H, brs) ppm; 13C NMR in Table 3; UV-Vis information in Table 5; FAB-HRMS: calcd for C38H48N4O6 [M]+ 656.3574, found 656.3589. 4Z,15Z)-2,two -(1,2-Ethenediyl)bis[5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2ylidine)methyl]-4-methyl-1H-pyrrole-3-butanoic acid] (4C36H46N4O6) To a solution of 20 mg homorubin acid 2 (0.03 mmol) in ten cm3 dry CH3)2SO 17 mg DDQ (0.083 mmol) was added at when, along with the solution was allowed to stir for 15 min. The reaction mixture was then poured into ice-water and stirred in an ice bath. The resulting solid was then removed by suction filtration, dissolved in ten cm3 CH2Cl2:CH3OH (60:40 by vol), and purified by flash column chromatography on silica gel using CH2Cl2:CH3OH (50:50 by vol) as eluent.1-Hydroxy-7-azabenzotriazole manufacturer The pure fractions had been evaporated in vacuo to obtain pure four.1-Bromo-2,3-dichloro-5-fluorobenzene Formula Yield: ten mg (47 ); m.PMID:22664133 p.: 273 (dec); 1H NMR ((CD3)2SO): = 1.ten (6H, t, J = 7.three Hz), 1.75 (4H, m), 1.80 (6H, s), 2.07 (6H, s), 2.36 (4H, t, J = 7.0 Hz), two.51 (4H, q, J = 7.3 Hz), two.79 (4H, t, J = 7.0 Hz), 5.96 (2H, s), 6.90 (2H, s), ten.16 (2H, s), ten.29 (2H, s), 12.04 (2H, brs) ppm; UV-Vis information in Table 5. (4Z,15Z)-9,9 -(1,2-Ethanediylidene)bis[3-ethyl-1,9-dihydro-2,7-dimethyl-1-oxodipyrrin-8propionic acid methyl ester] (5eC36H42N4O6) Inside a 50 cm3 round-bottom flask equipped with a magnetic stirrer was dissolved 40 mg homorubin dimethyl ester 1e (0.063 mmol) in 30 cm3 THF. To this solution was added 32 mg DDQ (0.130 mmol). The mixture was stirred for 20 min, then quenched with 75 cm3 water containing 100 mg ascorbic acid, and extracted with 50 cm3 CH2Cl2. The CH2Cl2 extract was washed with 20 cm3 aq. 10 NaHCO3, water (three ?20 cm3), and dried more than anhydrous Na2SO4. The CH2Cl2 was removed (rotovap), as well as the remaining solid was purified making use of radial chromatography (CH2Cl2:CH3OH, 97:three by vol), resulting in 5e as a violet strong. Yield: 30 mg (76 ); m.p.: 260 (dec); IR (KBr): V = 3436, 2954, 2919, 2355, 1701, 1648, 1625, 1601 cm-1; 1H NMR: = 1.20 (6H, t, J = 7.3 Hz), 1.95 (6H,.
