Ethyl Acetate → Ethyl 3-{3'-[(benzoylmethylamino)-methyl] biphenyl-4-yl}-2-methylpropionate

HRID 584898Notes

Reaction equation

HRID 584898 reaction equation
[CH3:1]/[C:2](=[CH:8]\[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22]C(C3C=CC=CC=3)=O)[CH:16]=2)=[CH:11][CH:10]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O:34][CH2:35][CH3:36])(=O)C>>[C:35]([CH2:36][NH:22][CH2:21][C:17]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:8][CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:10][CH:11]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:34])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 86591249ethyl (E)-2-methyl-3-(3'-{[(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)acrylate

Product 1

HCID 15550199Ethyl 3-{3'-[(benzoylmethylamino)-methyl] biphenyl-4-yl}-2-methylpropionate

Procedure

2.2 g (5.3 mmol) of ethyl (E)-2-methyl-3-(3′-{[(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)acrylate and 100 ml of ethyl acetate are introduced into a three-necked flask. The reaction medium is degassed, 450 mg of palladium-on-charcoal (10%) are added and the mixture is hydrogenated under atmospheric pressure for two hours. The reaction medium is filtered and evaporated, and the residue obtained is purified by chromatography on a column of silica eluded with a mixture of heptane and ethyl acetate (80/20). After evaporation of the solvents, 1.45 g (64%) of ethyl 3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-methylpropionate are collected in the form of an oil.

Workup

  1. customThe reaction medium is degassed
  2. addition450 mg of palladium-on-charcoal (10%) are added
  3. filtrationThe reaction medium is filtered
  4. customevaporated
  5. customthe residue obtained
  6. customis purified by chromatography on a column of silica
  7. additioneluded with a mixture of heptane and ethyl acetate (80/20)
  8. customAfter evaporation of the solvents, 1.45 g (64%) of ethyl 3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-methylpropionate
  9. customare collected in the form of an oil

Sources & evidence

ORD record
ord-eaf06a60981444c8aaa4077a68c025fa
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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