反应详情

温度

65 °C

To a solution of 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorbenzenesulfonic acid (3.0 g, 5.1 mmol) in DCM (15 mL) was added thionyl chloride (7.5 mL) and DMF (0.1 mL). The mixture was heated at 65° C. for 1 h then concentrated in vacuo and azeotroped with toluene (10 mL) and DCM (10 mL). The pale yellow foam was dissolved in DCM (15 mL) and was added dropwise to a solution of D-alanine methyl ester (2.9 g, 20.6 mmol) in 2M Na2CO3 (30 mL) with vigorous stirring. Upon complete addition the layers were separated and the organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with 0-70% ethyl acetate/hexane to afford a white foam (2.4 g, 77%). MS (EI) m/z 601.3 (M+).

1. concentrationthen concentrated in vacuo
2. customazeotroped with toluene (10 mL) and DCM (10 mL)
3. dissolutionThe pale yellow foam was dissolved in DCM (15 mL)
4. additionUpon complete addition the layers
5. customwere separated
6. dry with materialthe organics were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by flash chromatography
10. washeluting with 0-70% ethyl acetate/hexane