Methyl 4-([(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenylethenyl]benzyl}-oxy)phenethyl]amino}methyl)benzoate → Methyl 4-(((5-methoxy-5-oxopentyl)(2-((4-phenethylbenzyl)oxy)phenethyl)amino)methyl)benzoate

HRID 2110258Notes

Reaction equation

HRID 2110258 reaction equation
[CH3:1][O:2][C:3](=[O:44])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:33][C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1.[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:44])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:33][C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 22015012Methyl 4-([(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenylethenyl]benzyl}-oxy)phenethyl]amino}methyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 22015018Methyl 4-(((5-methoxy-5-oxopentyl)(2-((4-phenethylbenzyl)oxy)phenethyl)amino)methyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

781.8 mg (1.34 mmol) of methyl 4-({(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenyl-ethenyl]benzyl}oxy)phenethyl]amino}methyl)benzoate from Ex. 6 and 80.0 mg of 10% palladium on activated carbon in 10 ml of ethyl acetate are hydrogenated under atmospheric pressure. After 1 hour, the calculated amount of hydrogen has been taken up. The solution is filtered and the solvent distilled off under reduced pressure. The crude product is purified by chromatography over silica gel using the mobile phase cyclohexane/ethyl acetate=10:1.

Workup

  1. filtrationThe solution is filtered
  2. distillationthe solvent distilled off under reduced pressure
  3. customThe crude product is purified by chromatography over silica gel using the mobile phase cyclohexane/ethyl acetate=10:1

Sources & evidence

ORD record
ord-71b1d551a24a4530880b565554a94359
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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