HCID 67048388, compound → HCID 67048369, compound

HRID 1629846Notes

Reaction equation

HRID 1629846 reaction equation
[CH2:1]([N:4]([C:16](=[O:21])[CH2:17][CH2:18][CH:19]=[CH2:20])[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH3:15])C=C>C(=C1CCCC(P(Cl)(Cl)(C2CCCCC2)C2CCCCC2)C1=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)C1C=CC=CC=1.[Ru]>[N:4]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=2[CH3:15])[CH2:1][CH2:20][CH:19]=[CH:18][CH2:17][C:16]1=[O:21]

Participants

3

Reactant 1

HCID 67048388HCID 67048388, compound

Product 1

HCID 67048369HCID 67048369, compound

Reagents, catalysts & solvents 1

HCID 131726864HCID 131726864, compoundCatalyst

Procedure

150 mg (0.52 mmol) methyl 4-(allyl-pent-4-en-1-oyl-amino)-3-methyl-benzoate are dissolved in 110 ml degassed dichloromethane and rinsed for 30 minutes with argon. Then 88 mg (104 μmol) benzylidene-[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-dichloro-(tricyclohexylphosphine)-ruthenium (2nd generation Grubbs Catalyst) are added and the mixture is refluxed for 4.5 hours. Then it is evaporated down i. vac., the residue is applied to silica gel and purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 3:2).

Workup

  1. customdegassed dichloromethane
  2. washrinsed for 30 minutes with argon
  3. temperaturethe mixture is refluxed for 4.5 hours
  4. customThen it is evaporated down i
  5. custompurified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-c521ccdc83fb486dac62bbb038094a73
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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