Reacción #1956962

Ecuación de reacción

2,6-dichlorobenzaldehyde

Yb(OTf)3

MgSO4

phenyl vinyl sulfide

Methyl 3-(4-aminophenyl)-2-[(tert-butoxycarbonyl)amino]propanoate

methyl 3-(4-aminophenyl)-2-[(tert-butoxycarbonyl)amino]propanoate

→

methyl 2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-4-(phenylsulfanyl)-1,2,3,4-tetrahydro-6-quinolinyl]propanoate

Rendimiento 81.0%

Disolventes

CH3CN CH2Cl2

CH3CN CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter one night
2. 2
   Filtracióninsolubles are filtered
3. 3
   Otrothe solvents evaporated
4. 4
   OtroThe residue is purified by silica gel chromatography

Procedimiento

Methyl 3-(4-aminophenyl)-2-[(tert-butoxycarbonyl)amino]propanoate 4 (38.2 g) solubilized in a 50/50 mixture of CH3CN/CH2Cl2 is added, at room temperature, to a mixture of Yb(OTf)3 (0.05 equ.) and MgSO4 (3 equ.) in CH3CN/CH2Cl2 (50/50,400 ml). Solid 2,6-dichlorobenzaldehyde (1.1 equ.) is then added and after 2 h, phenyl vinyl sulfide (1.2 equ.) is added dropwise. After one night, insolubles are filtered and the solvents evaporated. The residue is purified by silica gel chromatography using hexane mixture/AcOEt 80/20 as eluent to give methyl 2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-4-(phenylsulfanyl)-1,2,3,4-tetrahydro-6-quinolinyl]propanoate 5.

Fuente