反应详情

A solution of (2-azidoethyl)carbamic acid t-butyl ester (1.22 g, 6.55 mmol) in methanol (60 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide on charcoal (1.22 g) at room temperature. After checking the completion of the reaction, the reaction mixture was filtered, and the filtrate concentrated under reduced pressure. To a solution of the obtained crude product in methylene chloride (60 ml) were added chloroformic acid p-nitrobenzyl ester (2.12 g, 9.8 mmol) and triethylamine (1.37 ml, 9.8 mmol) in an ice bath, and the reaction mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (3:1) as the eluant to afford (2-t-butoxycarbonylaminoethyl)carbamic acid p-nitrobenzyl ester (1.46 g, yield 66%) as a white solid.

1. customthe completion of the reaction
2. filtrationthe reaction mixture was filtered
3. concentrationthe filtrate concentrated under reduced pressure
4. customTo a solution of the obtained crude product in methylene chloride (60 ml)
5. customthe completion of the reaction
6. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by chromatography on a silica gel column