Tetrahydrofuran → Diethyl 2-(3'-{[methyl-(1-phenylmethanoyl)-amino]methyl}biphenyl-4-ylmethyl)malonate

HRID 584913Notes

Reaction equation

HRID 584913 reaction equation
[CH3:1][N:2]([CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C1COCC1>CO>[CH3:1][N:2]([CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:23]=2)[CH:15]=[CH:16][CH:17]=1)[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 22341469Diethyl 2-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-ylmethylene)malonate

Product 1

HCID 22341493Diethyl 2-(3'-{[methyl-(1-phenylmethanoyl)-amino]methyl}biphenyl-4-ylmethyl)malonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 mg (1.5 mmol) of diethyl 2-(3′-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-ylmethylene)malonate, 7 ml of THF and 1 ml of methanol are introduced into a three-necked flask under a stream of nitrogen. The reaction medium is degassed, 80 mg of palladium-on-charcoal (5%) are introduced and the mixture is hydrogenated under atmospheric pressure at room temperature for 20 hours. The reaction medium is filtered through Celite and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (80/20). After evaporation of the solvents, 450 mg (63%) of the desired product are collected.

Workup

  1. customThe reaction medium is degassed
  2. addition80 mg of palladium-on-charcoal (5%) are introduced
  3. filtrationThe reaction medium is filtered through Celite
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (80/20)
  8. customAfter evaporation of the solvents, 450 mg (63%) of the desired product
  9. customare collected

Sources & evidence

ORD record
ord-d3bc1959691e48688917894e1f76aa21
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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