N-9-fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine

1365284-58-7

150308-80-8

The general procedure for the synthesis of N-fluorenylmethoxycarbonyl-3-[[(4-methoxyphenyl)methyl]selenyl]-L-alanine from the compound (CAS: 1365284-58-7) was as follows: a mixture of raw material 14 (790 mg, 1.5 mmol) and trimethyltin hydroxide (989 mg, 5.5 mmol) was dissolved in anhydrous 1,2-dichloroethane ( 15 mL). The reaction mixture was stirred at 35 °C overnight. Upon completion of the reaction, the mixture was filtered and the filtrate was evaporated to remove the solvent. The resulting crude product was purified by silica gel column chromatography with an eluent ratio of hexane:EtOAc = 2:1 to 0:1 to give product 15 as a colorless oil or white solid (702 mg, 91% yield). The spectral data of product 15 were in agreement with those reported in the literature37 and its purity was confirmed by 1H NMR and HPLC analyses.1H NMR (CDCl3) data were as follows: δ 2.98 (2H, m, β-H), 3.78 (3H, s, p-OMe), 3.79 (2H, s, CH2), 4.26 (1H, t, JHH 6.8 Hz, Fmoc-CH ), 4.45 (1H, d, JHH 6.7 Hz, Fmoc-CH2), 4.70 (1H, m, α-H), 5.54 (1H, d, JHH 7.8 Hz, NH), 6.83 (2H, d, JHH 8.4 Hz, ArH), 7.20 (2H, d, JHH 8.3 Hz, ArH), 7.33 (2H, m, ArH ), 7.42 (2H, m, ArH), 7.63 (2H, t, JHH 6.7 Hz, ArH), 7.78 (2H, m, ArH).13C NMR (CDCl3) data were as follows: δ 25.1, 27.7, 47.1, 53.6, 55.3, 67.3, 114.1, 120.0, 125.1, 127.1, 127.8, 130.0, 141.3, 143.6, 158.7. 77Se NMR (CDCl3) data are as follows: δ 216.7.