C(Cl)CCl.[C-:5]1([C:10]([OH:12])=O)[CH:9]=[CH:8][CH:7]=[CH:6]1.[CH-:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:18].ON1C(=O)CCC1=O.[Cl-].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][S:35][CH2:36][CH2:37][NH3+:38].CCN(CC)CC>C(Cl)Cl>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][S:35][CH2:36][CH2:37][NH:38][C:10]([C:5]1[CH-:6][CH:7]=[CH:8][CH:9]=1)=[O:12].[CH-:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:18]EDC (213 mg, 1.1 mmol) was added to a solution of ferrocenecarboxylic acid (232 mg, 1.0 mmol) and N-hydroxysuccinimide (128 mg, 1.1 mmol) dissolved in 20 mL of CH2Cl2. The solution was stirred at room temperature for 5 h and concentrated. The crude residue was dissolved in 8 mL of DMF and 2-(pyridin-2-yldisulfanyl)-ethyl-ammonium chloride (222 mg, 1.0 mmol) was added followed by Et3N (0.14 mL, 1.0 mmol). After stirring for 48 h, the solvent was evaporated in vacuo. The crude residue was purified by flash chromatography (gradient: hexanes/EtOAc, 1:1, v/v to EtOAc) to afford 113 mg (28% over 2 steps) of 12. 1H NMR 400 MHz (CDCl3) d 8.56 (m, 1H), 7.61 (m, 1H), 7.52 (m, 1H), 7.43 (t, J=6.8 Hz, 1H), 7.15 (m, 1H), 4.75 (m, 2H), 4.34 (m, 2H), 4.20 (s, 5H), 3.63 (q, J=6.0 HZ, 2H), 2.98 (t, J=6.0 Hz, 2H).
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