反应详情

温度

80 °C

3-[2-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester: To a solution of 161.0 g (561.8 mmol) of material from Part A, 58.0 g (674.2 mmol) of methyl acrylate and 170.5 g (1685.4 mmol) of triethylamine in 800 mL of N,N-dimethylformamide was added 7.9 g (11.2 mmol) of dichlorobis(triphenylphosphine)palladium(II) and the mixture was heated at 80° C. for 32 hr. The mixture was cooled, diluted with 1000 mL of ethyl acetate and washed with 10% aqueous sodium bisulfate. The aqueous portion was extracted three times with ethyl acetate and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in a small amount of dichloromethane and filtered through 7 in. of silica gel in a 2 L sintered glass funnel eluting with 25% ethyl acetate/hexanes. The eluant was concentrated in vacuo and recrystallized from ethyl acetate/hexanes to afford 116.9 g (71%) of the title compound.

1. temperatureThe mixture was cooled
2. washwashed with 10% aqueous sodium bisulfate
3. extractionThe aqueous portion was extracted three times with ethyl acetate
4. dry with materialthe combined organics were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in a small amount of dichloromethane
8. filtrationfiltered through 7 in
9. washof silica gel in a 2 L sintered glass funnel eluting with 25% ethyl acetate/hexanes
10. concentrationThe eluant was concentrated in vacuo
11. customrecrystallized from ethyl acetate/hexanes