L-Phenylalanine → HCID 11808095, compound

Participants

Reaction Steps

N3(L)PheOH (1SL) was synthesized from L-phenylalanine essentially by the procedure of Lundquist and Pelletier.17 N3(L)PheOH (1.08 g, 5.7 mmol) was dissolved in anhydrous DMF (40 mL). HOBt (0.87 g, 5.7 mmol) was then added, followed by DCC (1.17 g, 5.7 mmol). Once precipitate was observed in the reaction, benzyl amine (0.62 mL, 5.7 mmol) was added. The reaction was allowed to stir under Ar(g) for 3 h. The resulting precipitate (DCU) was removed by filtration, and the filtrate was concentrated under reduced pressure to give a yellow oil. This oil was purified by flash chromatography (silica gel, 35% v/v/ethyl acetate in hexanes). N3(L)Penh (48-L) was isolated as an off-white solid in 90% yield. The procedure was repeated with D-phenylalanine to give N3(D)Penh products (D and L enantiomers) are identical. N3(L)Penh (48-L) 1H NMR (500 MHz, CDCl3 δ 7.31-7.12 (m, 8H), 7.11 (m, 2H), 6.55 (bus, 1H), 4.38 (m, 2H), 4.22 (did, J=7.8, 4.6 Hz, 1H), 3.34 (did, J=14.0, 4.5 Hz, 1H), 3.07 (did, J=14.1, 7.5 Hz, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ 168.30, 137.35, 135.96, 129.51, 128.61, 128.66, 128.61, 128.55, 127.70, 127.68, 127.66, 127.57, 127.16, 65.40, 43.41, 38.41 ppm; MS (ESI) m/z 303.1235 (MNa+[C16H16N4ONa]=303.1222).

Provenance & Evidence