4-Ethoxy-3-methoxyphenethylamine → N-[2-(4-Ethoxy-3-methoxyphenyl)ethyl]-3-[2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]benzamide

Solutions of 3-{2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxy methylphenyl)ethylamino]-2-methylpropyl}benzoic acid (preparation 37) (90 mg, 0.19 mmol) in N,N-dimethylacetamide (1 mL) and 0-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (61 mg, 0.16 mmol) in N,N-dimethylacetamide (0.5 mL) were added to a solution of 4-ethoxy-3-methoxyphenethylamine (37 mg, 0.19 mmol) in N,N-dimethylacetamide (0.5 mL). The resulting mixture was stirred for 72 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (4 mL) and saturated sodium hydrogen carbonate solution (1 mL). The mixture was then filtered through a phase separation tube and the organic solution was concentrated in vacuo. The residue was dissolved in dimethylsulfoxide (700 μL), triethylamine trihydrofluoride (30 μL, 0.19 mmol) was added and the mixture was stirred at room temperature for 72 hours. The reaction mixture was then purified directly by HPLC using a Phenomenex Luna C18 system, eluting with water/0.05% diethylamine:acetonitrile, 5:95 to 95:5, to afford the title compound in 30% yield (30.9 mg).

1. customThe solvent was removed in vacuo
2. customthe residue was partitioned between dichloromethane (4 mL) and saturated sodium hydrogen carbonate solution (1 mL)
3. filtrationThe mixture was then filtered through a phase separation tube
4. concentrationthe organic solution was concentrated in vacuo
5. dissolutionThe residue was dissolved in dimethylsulfoxide (700 μL)
6. stirringthe mixture was stirred at room temperature for 72 hours
7. customThe reaction mixture was then purified directly by HPLC
8. washeluting with water/0.05% diethylamine

ORD 기록

ord-ddaaa135e0cd40428d288b74d9356b3a

출처 데이터셋

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07629358B2