Piperidine → N5-(4-(2,2-bis(diallylphosphoryl)ethyl)phenyl)-L-glutamine

Participants

Reaction Steps

Fmoc-protected compound 105 (431 mg, 0.51 mmol) was treated with a 5% v/v solution of piperidine in DMF (2.5 mL). After stirring for 2.5 h, the reaction mixture was concentrated to dryness and purified by silica gel chromatography on a Biotage™ flash chromatography system using a gradient of 0-10% methanol in CH2Cl2. Compound 106 was obtained as a colorless oil (246 mg, 77%). 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.82-1.91 (m, 1H), 2.16-2.24 (m, 1H), 2.45-2.60 (m, 2H), 2.71 (tt, J=23.9, 6.2 Hz, 1H), 3.24 (dt, J=16.6, 6.2 Hz, 2H), 4.42 (dd, J=8.8, 4.5 Hz, 1H), 4.47-4.61 (m, 8H), 5.19-5.22 (m, 4H), 5.29-5.35 (m, 4H), 5.83-5.94 (m, 4H), 7.21 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.3 Hz, 2H), 8.57 (bs, 1H).

Provenance & Evidence