反应详情

To a solution of 4-[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)phenyl]butanoic acid (250 mg) in N,N-dimethylformamide (5.00 mL) were added tert-butyl O-tert-butyl-L-tyrosinate hydrochloride (152 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (88.5 mg), 1H-benzotriazol-1-ol (62.4 mg), and triethylamine (0.0643 mL), followed by stirring at room temperature overnight. To a reaction solution was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl N-{4-[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)phenyl]butanoyl}-O-tert-butyl-L-tyrosinate (327 mg).

1. extractionfollowed by extraction with ethyl acetate
2. washThe organic layer was washed with water
3. dry with materiala saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)