反应详情

温度

50 °C

TBDMSCl (1.01 g, 6.72 mmol), DMAP (0.19 g, 1.52 mmol) and pyridine (0.97 g, 12.2 mmol) were added to a stirred solution of FMOC-isoserine (1.00 g, 3.05 mmol) in DMF (20 mL). The reaction mixture was heated at 50° C. for 18 hrs. Water (10 mL) was added and the reaction mixture was concentrated in vacuo. DCM and HCl (0.5 M) were added and the two phases were separated. The aqueous phase was extracted two times with DCM. The organic extracts were combined concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with a gradient consisting of 20-100% EtOAc in heptane) to give the title compound (1.3 g). 1H NMR (500 MHz, CDCl3) δ 7.76 (d, 2H), 7.59 (m, 2H), 7.40 (t, 2H), 7.30 (m, 2H), 5.14 (br s, 1H), 4.29 (m, 4H), 3.53 (m, 2H), 0.91 (s, 9H), 0.10 (s, 6H).

1. concentrationthe reaction mixture was concentrated in vacuo
2. additionDCM and HCl (0.5 M) were added
3. customthe two phases were separated
4. extractionThe aqueous phase was extracted two times with DCM
5. concentrationThe organic extracts were combined concentrated in vacuo
6. customThe residue was purified with column chromatography (silica gel
7. washeluting with a gradient