2,6-Dichlorobenzaldehyde → Methyl 3-[2-(2,6-dichlorophenyl)-4-phenylsulfanyl-1,2,3,4-tetrahydroquinolin-6-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

HRID 1869780Notes

Reaction equation

HRID 1869780 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].[O-]S([O-])(=O)=O.[Mg+2].[Cl:53][C:54]1[CH:61]=[CH:60][CH:59]=[C:58]([Cl:62])[C:55]=1[CH:56]=O.[CH:63]([S:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)=[CH2:64]>CC#N.C(Cl)Cl>[C:18]([O:17][C:15]([NH:14][CH:9]([CH2:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][CH:56]([C:55]1[C:54]([Cl:53])=[CH:61][CH:60]=[CH:59][C:58]=1[Cl:62])[CH2:64][CH:63]2[S:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 5

HCID 67372,6-DichlorobenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 74572Phenyl Vinyl SulfideHCID 2733225Ytterbium triflateHCID 22227788Methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Product 1

HCID 11456054Methyl 3-[2-(2,6-dichlorophenyl)-4-phenylsulfanyl-1,2,3,4-tetrahydroquinolin-6-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoateYield 81%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent2×

Procedure

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.

Workup

  1. waitAfter one night
  2. filtrationinsolubles are filtered
  3. customthe solvents evaporated
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-dfc48f339da447d6bd92e996368ca0b0
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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