反应详情

tert-butyl (1S)-3-bromo-1-(3,5-difluorobenzyl)-2-oxopropylcarbamate (III, EXAMPLE 1, 1 equivalent) is dissolved in isopropanol and treated with 3-methoxybenzylamine (VI, 5 equivalents). The reaction is heated at reflux for 2 hours and monitored by TLC for disappearance of the ketone (III). Upon completion, the reaction is concentrated to dryness under reduced pressure and partitioned between equal parts water and ethyl acetate. The organic phase is extracted, washed two additional times with water, then saline, then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography on silica gel to give the title compound.

1. temperatureThe reaction is heated
2. temperatureat reflux for 2 hours
3. concentrationUpon completion, the reaction is concentrated to dryness under reduced pressure
4. custompartitioned between equal parts water and ethyl acetate
5. extractionThe organic phase is extracted
6. washwashed two additional times with water
7. dry with materialsaline, then dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe crude material is purified by column chromatography on silica gel