Dicyclohexylcarbodiimide → HCID 178520597, compound

Participants

Reaction Steps

Compound 4 (0.175 g, 0.81 mmol), N,N′-dicyclohexylcarbodiimide (0.169 g, 0.82 mmol), 1-hydroxybenzotriazole (0.126 g, 0.82 mmol), and 11-mercaptoundecanoic acid (0.179 g, 0.82 mmol) were combined in degassed acetone (12 mL). The solution was stirred at r.t. for 18 h under an atmosphere of Ar. The reaction mixture was concentrated in vacuo and dissolved in dichloromethane (100 mL). After washing with water (3×50 mL), the organic phase was dried over Na2SO4, filtered, and concentrated to a crude residue that was purified by column chromatography on silica gel (2:3, EtOAc:hexanes) to yield the pure product as a pale orange solid (0.288 g, 0.69 mmol, 85%). 1H NMR (CDCl3): δ 1.25-1.38 (m, 13H, (CH2)6+SH), 1.57-1.66 (m, 4H, COCH2CH2+CH2CH2SH) 2.17 (t, JH-H=7.8 Hz, 2H, COCH2), 2.51 (psuedo dt, JN-H=7.3 Hz, 7.4 Hz, 2H, CH2SH), 4.13-4.15 (m, 4H, NHCH2+ferrocene-H), 4.16 (bs, 5H, ferrocene-H), 4.18 (pt, 2H, ferrocene-H), 5.56 (bs, 1H, NH). 13C{1H} NMR (CDCl3): δ 24.9, 26.0, 28.6, 29.2, 29.5, 29.5, 29.6, 29.6, 34.2, 37.0, 39.0, 68.4, 68.5, 68.8, 85.0, 172.6.

Provenance & Evidence