Acetic Acid → a-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-[(3-phenyl)-2-propenyl]amino-benzyl alcohol

In methanol (15 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.6 g) produced in Example (1) and cinnamaldehyde.(0.5 g). To the solution was added acetic acid (0.11 g). To the mixture was added, while stirring at room temperature, cyano sodium borohydride (0.12 g). The reaction mixture was stirred for 40 minutes at 60° C., which was concentrated. The concentrate was subjected to extraction by the addition of water (30 ml) and ethyl acetate (50 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give a-(3-tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-[(3-phenyl)-2-propenyl]amino-benzyl alcohol (0.8 g) as a colorless oily product.

1. additionTo the mixture was added
2. stirringThe reaction mixture was stirred for 40 minutes at 60° C.
3. concentrationwhich was concentrated
4. extractionThe concentrate was subjected to extraction by the addition of water (30 ml) and ethyl acetate (50 ml)
5. washThe organic layer was washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. distillationThe solvent was distilled off
8. customthe residue was purified by means of a silica gel column chromatography

ORD 기록

ord-51f220a8d14a4fdcba5bdfe5cfafbddc

출처 데이터셋

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06352982B1