Diisopropylethylamine → N2-(9-fluorenylmethoxycarbonyl)-N5-(bis(diallylphosphoryl)methyl)-L-glutamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of Fmoc-Glu-Ot-Bu (646 mg, 1.52 mmol) in DMF (5 mL) at 0° C. was added DIEA (529 μL, 3.04 mmol) and HBTU (576 mg, 1.52 mmol). After stirring for 15 min at 0° C., amino bisphosphonate 96 (533 mg, 1.52 mmol) in DMF (2.6 mL) was added and stirring was pursued for 5 h at 0° C. The reaction mixture was diluted with CH2Cl2, washed with H2O, 0.5 N HCl solution, saturated NaHCO3 solution and saturated NaCl solution. The organic layer was dried over MgSO4, filtered and concentrated to dryness. The crude product was purified by silica gel chromatography on a Biotage™ flash chromatography system using a gradient of 0-5% methanol in CH2Cl2. Compound 97 was obtained as a light yellow oil (898 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.82-1.91 (m, 1H), 2.15-2.32 (m, 3H), 4.20-4.27 (m, 2H), 4.38-4.47 (m, 2H), 4.58-4.68 (m, 8H), 5.20-5.26 (m, 5H), 5.34-5.40 (m, 4H), 5.54 (d, J=7.9 Hz, 1H), 5.87-5.98 (m, 4H), 6.59 (bs, 1H), 7.30-7.34 (m, 2H), 7.41 (t, J=7.5 Hz, 2H), 7.61 (d, J=7.5 Hz, 2H), 7.77 (d, J=7.5 Hz, 2H).

Herkunft & Nachweise