Trimethylsilyl iodide → HCID 9796603, compound

Participants

Reaction Steps

A solution of 100 mg (0.2 mmol) of (±)-diethyl 3-(benzyloxycarbonylamino)pentadecylphosphate (from Example 27, Step C) in 1 mL of CH2Cl2 was treated with 0.11 mL (0.8 mmol) of iodotrimethylsilane then stirred at rt for 1 h. The reaction was quenched with 1 mL of methanol, stirred at rt for 15 min then concentrated. The resulting oil was dissolved in 0.5 mL of EtOAc, diluted with 5 mL of hexanes and. sonicated for 1 min. The suspension was filtered and dried to give 68 mg of the title compound: 1H NMR (500 MHz) δ 3.22-3.30 (m, 1H), 1.76-2.01 (m, 4H), 1.56-1.70 (m, 2H), 1.26-1.46 (m, 20H), 0.89 (t, J=6.9 Hz, 3H); ESI-MS 308.2 (M+H).

Provenance & Evidence