methyl 3-(4-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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. After one night insolubles are filtered the solvents evaporated The residue is purified by silica gel chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl 2-[(tert-butoxycarbonyl)amino]-3-(4 nitrophenyl)propanoate 3 (69.4 g) and NH4HCO2 (6.5 equ.) in CH3OH (20 ml/g) is added 5% Pd/C (15% in weight, 10 g). The temperature rises to 40° C. and then decreases. After stirring for 2 h at room temperature, the solution is filtered over celite and the solvent is evaporated. The residue is diluted in AcOEt and washed 3 times with water. The organic phase is dried over MgSO4 and evaporated to dryness. No further purification is needed. rises to 40° C. the solution is filtered over celite the solvent is evaporated The residue is diluted in AcOEt washed 3 times with water The organic phase is dried over MgSO4 evaporated to dryness No further purification