HCID 67186015, compound → HCID 67188167, compound

HRID 735930Notes

Reaction equation

HRID 735930 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]([N:7]([CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)=[O:6])[CH3:2]>CCOC(C)=O.CCO.CCOC(C)=O.O=[Pt]=O>[CH2:1]([O:3][C:4](=[O:27])[C:5]([N:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1)[CH2:18][C:19]1[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=1)=[O:6])[CH3:2]

Participants

5

Reactant 1

HCID 67186015HCID 67186015, compound

Product 1

HCID 67188167HCID 67188167, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

A suspension of PtO2 (250 mg) in EtOAc (5 mL) was added to a solution of ethyl[(3,5-dichlorobenzyl) (4-nitrobenzyl)amino](oxo)acetate (2.00 g, 4.86 mmol) in EtOH/EtOAc (2/1, 90 mL) under H2 (1 atm). The reaction mixture was stirred vigorously at rt for 30 min. The reaction mixture was filtered over a pad of Celite and silica gel to remove the catalyst. The solvents were removed under reduced pressure. The residue was purified by flash chromatography over silica gel (c-Hex/EtOAc 2/1) to give the title compound as a pale yellow oil (1.21 g, 61%). 1H NMR (CDCl3, 300 MHz) δ 7.31-7.05 (m, 5H), 6.71 (m, 2H), 4.39 (m, 4H), 4.25 (br s, 2H), 1.36 (m, 3H). HPLC (Condition A), Rt: 3.4 min (HPLC purity: 94.1%).

Workup

  1. filtrationThe reaction mixture was filtered over a pad of Celite and silica gel
  2. customto remove the catalyst
  3. customThe solvents were removed under reduced pressure
  4. customThe residue was purified by flash chromatography over silica gel (c-Hex/EtOAc 2/1)

Sources & evidence

ORD record
ord-a4772267802348d3ad55d8213ec3cf84
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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