x FcCH). Anal. Calcd for C19H17FeNO4, xFcCH)CH2), 65.5 (2 x FcCH) ,
2948(8) Å, ? = 11419(13) Å 3 . Z = 4, d = 1.551 g.cm -3 , ? = 0.918 mm -1 . A final refinement on F 2 with 3871 unique intensities and 247 parameters converged at wR(F 2 ) = 0.0680 (R(F) = 0.0289) for 3261 observed reflections with I > 2?(I) CCDC 1584018. 1'-[((Fluoren-9-yl)methoxycarbonyl)amino]ferrocene-1- carboxylic acid (8) The general procedure 1 using 1'- azidocarbonylferrocene-1-carboxylic acid (4, 239 mg, 0.8 mmol) and (9H-fluoren-9-yl)methanol (SI4, 392 mg, 2.0 mmol) afforded the title product as a yellow solid (185 mg, 49%). mp 128-130 °C (decomp.); IR (ATR): 2957 (br), H NMR (500 MHz, DMSO-d 6 ) ? 11.99 (s, 1H, CO2H), 9.00 (s, 1H, NH), 7.91 (d, J = 7.0 Hz, 2H, 2 x AcCH) x ArCH), pp.736-174, 1080. ,
5 equiv) were added to a solution of the corresponding protected 1'-aminoferrocene-1-carboxylic acid (1.0 equiv) in anhydrous DCM (0.1 M) After 5h stirring at room temperature, volatiles were removed under vacuum to give the crude product, This was purified by column chromatography on silica, eluting with EtOAc/heptane, p.50 ,
) afforded the title product as an orange solid (276 mg, 62%) and 1'-((tertbutoxycarbonyl )amino)ferrocene-1-carboxylic anhydride (14, 23 mg, 7%) as a red solid. 1'-((tert-Butoxycarbonyl)amino)ferrocene- 1-carboxylic anhydride (14): mp 165-167 °C (lit. 24 167-168 °C); IR (ATR): 3316, H NMR (500 MHz, CDCl3) ? 6.36 (s, 2H, 2 x NH), 4.82 (s, 4H, 4 x FcCH), 4.68 (s, 4H, 4 x FcCH), 4.56 (s, 4H, 4 x FcCH), 4.08 (s, 4H, 4 x fcCH) x C=Oanhydride), 153.5 (C=Ocarbamate), 99.0 (2 x FcC) x C(CH3)3), pp.755-756, 0905. ,
x CH2) Anal. Calcd for C20H22FeN2O6: C, 54.32; H, 5.01; N, 6.33) K, monoclinic P 21/c, a = 21, 28.0 (C(CH3)3), 2036. ,
22 (s, 2H, 2 x FcCH), 2.84 (s, 4H, 2 x CH2) ,
x CH2) Anal. Calcd for C23H20FeN2O6: C, 58.00; H, 4.23; N, 5.88. Found: C, 58.09; H, 4.29; N, 5.99. 2,5-Dioxopyrrolidin-1-yl 1'-[((fluoren-9- yl)methoxycarbonyl)amino]ferrocene-1-carboxylate (12) The general procedure 2 using 1'-[((fluoren-9- yl)methoxycarbonyl)amino]ferrocene-1-carboxylic acid (8, 56.1 mg, 0.12 mmol, 1.0 equiv), N-hydroxysuccinimide (34.5 mg, 0.18 mmol, 1.5 equiv) and EDC.HCl (20.7 mg, 0.18 mmol, 1.5 equiv) afforded the title product as an orange solid (59.9 mg, 88.5%). mp 80-84 °C; IR (ATR): 325385 (s, 2H, 2 x FcCH), 4.63 (s, 2H, 2 x FcCH), 4.50 (s, 4H x CH2). Anal(allyloxycarbonyl)amino)ferrocene -1- carboxylate (13). The general procedure 2 using 1'- ((allyloxycarbonyl)amino)ferrocene-1-carboxylic acid5 equiv) afforded the title product as an orange solid, H NMR (500 MHz, DMSO-d 6 ) ? 8.98 (br s, 1H, NH), 7.91 (d, J = 6.9 Hz, 2H, 2 x ArCH) x ArC) x ArCH), 127.6 (2 x ArCH), 127.0 (2 x ArCH), 125.0 (2 x ArCH) x ArCH), 99.2 (FcC), 74.9 (2 x FcCH) x FcCH), 69.9 (2 x FcCH), 65.2 (CH2), 63.6 (FcC) 1H, HC=CHH), 4.89 (s, 2H, 2 x FcCH), 4.63 (s, 2H, 2 x FcCH), 4.59 (s, 2H, 2 x FcCH), 4.57 (s, 2H, CH2), 4.22 (s, 2H, 2 x FcCH) x CH2); 13 C NMR (125.7 MHz, DMSO-d 6 ) ? 170.6 (C=Osuccinimidyl) x FcCH) x FcCH), pp.741-742, 0933. ,
x CH2) Anal. Calcd for C19H18FeN2O6: C, 53.54; H, 4.26; N, 6.57. Found: C, 53.63; H, 4.38; N, 6.68. N-methyl 1'-((tert-butoxycarbonyl)amino)ferrocene-1- carboxamide (15) Under argon equiv) was added to a solution of, pp.61-66 ,
Anal. Calcd for C17H22FeN2O3: C, 57.00; H, 6.19, CH3)3) ,
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