反应详情

Benzylamine (0.270 g, 2.52 mmol) was coupled to Fmoc-Thr(tBu)-OH (S29, 1.00 g, 2.52 mmol) using the standard HATU coupling procedure. The reaction was diluted with Et2O (150 mL), and washed with 10% citric acid solution (60 mL), water (3×60 mL), and brine (60 mL). The organic layer was dried (MgSO4), filtered, and concentrated by rotary evaporation. The crude product was purified using flash chromatography (15% EtOAc/hexanes) to afford S30 as a white solid (1.20 g, 98% yield). Rf 0.53 (1:1 EtOAc/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=7.5 Hz, 2H), 7.61 (d, J=7.4 Hz, 2H), 7.44-7.27 (m, 9H), 6.06 (d, J=4.6 Hz, 2H), 4.50 (dd, J=7.8, 5.7 Hz, 2H), 4.44-4.37 (m, 2H), 4.27-4.14 (m, 3H), 1.24 (s, 9H), 1.04 (d, J=6.5 Hz, 3H); HRMS m/z calcd for C30H34N2NaO4 [MNa+] 509.2416, found 509.2226.

1. washwashed with 10% citric acid solution (60 mL), water (3×60 mL), and brine (60 mL)
2. dry with materialThe organic layer was dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated by rotary evaporation
5. customThe crude product was purified