62% |
With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 12h; |
Example 1 - Preparation of ferrocene modified phospholipid (3)[0064] Ferrocene modified phospholipid (FC-DSP) was prepared in the following manner: triethylamine (0.077 mmol, 0.01 ml_, 1.4 eq) and N,N-dicyclohexylcarbodiimide (0.077 mmol, 15.9 mg, 1.4 eq) were added to a solution that contained 1 ,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (0.055 mmol, 35 mg, 1.0 eq) and <strong>[1287-16-7]ferroceneacetic acid</strong> (0.077 mmol, 18.8 mg, 1.4 eq) in anhydrous DCM (1.5 ml_). The reaction was stirred overnight, until N MR indicated conversion to the coupling was completed. The solution was concentrated under vacuum and then was purified on iatrobeads gel chromatography ( 10% MeOH : DCM). A dark-brown oil (29.4 mg, 0.0341 mmol) was obtained (62% yield). H N MR (300 MHz, CDCI3) delta 7.04 (br, 1 H), 5.23 (br, 1 H), 4.37 (br, 1 H), 4.22 (br, 2H), 4.12 (br, 5H), 3.94 (br, 2H), 3.49 (br, 4H), 3.28 (br, 2H), 3.05 (br, 4H), 2.28 (br, 4H), 1.58 (br, 4H), 1.25 (br, 40H), 0.87 (t, J = 6.5 Hz, 6H).3P NMR (122 MHz, CDCI3) delta 0.15 (s).3C N MR (75 MHz, CDCI3) delta 173.60 (s), 173.21 (s), 70.56 (s), 69.26 (s), 68.92 (s), 68.14 (s), 62.82 (s), 45.87 (s), 34.44 (s), 34.25 (s), 32.05 (s), 29.80 (s), 29.65 (s), 29.49 (s), 29.29 (s), 25.02 (s), 22.81 (s), 14.24 (s), 8.73 (s). HRMS (ESI): Calc. for C45H76FeN09P (M+H)+: 862.4680; found : 862.4624. |