反应详情

A mixture of (S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid (2.7 g, 0.010 mol), 4-fluoro-benzene-sulfonyl chloride (2.0 g, 0.010 mol), and sodium carbonate (2.2 g, 0.020 mol) in a mixture of tetra-hydrofuran (20 mL) and water (20 mL) was stirred at room temperature for 3 days. The reaction mixture was partitioned between ethyl acetate and 1 M hydrochloric acid. The organic layer was washed with saturated sodium chloride solution, dried (MgSO4), and rotary-evaporated under reduced pressure to give an oil. The oil was chromatographed on silica gel (445 g, 230-400 mesh) eluting with dichloromethane-methanol (20:1), and the fractions containing product were rotary-evaporated to give a solid. The solid was recrystallized from toluene to give the title compound as a light yellow solid; yield 0.22 g (5%), mp=138-139° C.

1. customThe reaction mixture was partitioned between ethyl acetate and 1 M hydrochloric acid
2. washThe organic layer was washed with saturated sodium chloride solution
3. dry with materialdried (MgSO4)
4. customrotary-evaporated under reduced pressure
5. customto give an oil
6. customThe oil was chromatographed on silica gel (445 g, 230-400 mesh)
7. washeluting with dichloromethane-methanol (20:1)
8. additionthe fractions containing product
9. customwere rotary-evaporated
10. customto give a solid
11. customThe solid was recrystallized from toluene