Trichloroethanol → Fmoc-Ser(OtBu)-OTce

Participants

Reaction Steps

Fmoc-Ser(tBu)-OH (1 g, 2.6 mmol) was dissolved in CH2Cl2 (7 mL). DMAP (0.15 g, 1.3 mmol, 0.5 equiv) and 2,2,2-trichloroethanol (Tce) (0.3 mL, 3.1 mmol, 1.2 equiv) were first added, and then DCC (0.63 g, 3.1 mmol, 1.2 equiv) in CH2Cl2 (2.5 mL) was added under N2 atmosphere at 0° C. The reaction mixture was allowed to stir for 18 h at room temperature. The organic reaction was cooled to 0° C., filtered and the filtrate was concentrate in vacuo. The resulting crude was dissolved in EtOAc (7 mL) and washed with 10% aqueous citric acid (2×10 mL), saturated aqueous NaHCO3 (2×10 mL) and brine (2×10 mL), dried (MgSO4), and concentrated in vacuo to give Fmoc-Ser(OtBu)-OTce (1.34 g), which was used without further purification.

Provenance & Evidence