反应详情

A solution of tert-butyl 2-(3-{[tert-butyl(dimethyl)silyl]oxy }phenyl)-4-(5-chloro-2-fluorophenyl)-2,5dihydro-1H-pyrrole-1-carboxylate (3-2, 276 mg, 0.683 mmol, 1 equiv), triethylamine (277 mg, 2.73 mmol, 4 equiv), PYBOP (711 mg, 1.37 mmol, 2 equiv) and 2-[(tert-butoxycarbonyl)amino]-2-methylpropanoic acid (278 mg, 1.37 mmol, 2 equiv) in in DMP (10 mL) was warmed at 60° C. for 18 h. The solution was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography. Elution with 10% ethyl acetate/hexanes to 20% ethyl acetate/hexanes gave tert-butyl 2-[2-(3{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(5-chloro-2-fluorophenyl)-2,5-dihydro-1H-pyrrol-1yl]-1,1-dimethyl-2-oxoethylcarbamate (3-3) as a pale yellow gum. LRMS n/z (M+H) 588.9 found, 589.0 required.

1. concentrationThe solution was concentrated
2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
3. washThe organic layer was washed with brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. customThe residue was purified by flash column chromatography
7. washElution with 10% ethyl acetate/hexanes to 20% ethyl acetate/hexanes