4-[But-3-enyl-(2,4-dimethoxybenzyl)-carbamoyl]-pent-4-enoic acid methyl ester → HCID 16720333, compound

HRID 2240594Notes

Reaction equation

HRID 2240594 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]([C:8](=[O:25])[N:9]([CH2:21][CH2:22][CH:23]=C)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[O:19][CH3:20])=C>C(Cl)Cl.[Ru]>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[C:8](=[O:25])[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])[CH2:21][CH2:22][CH:23]=1

Participants

4

Reactant 1

HCID 167203324-[But-3-enyl-(2,4-dimethoxybenzyl)-carbamoyl]-pent-4-enoic acid methyl ester

Product 1

HCID 16720333HCID 16720333, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

130 mg of the compound (c) (0.360 mM) prepared by the above Step 2 was added to the catalyst solution containing 20 mg of ruthenium (0.024 mM) dissolved in CH2Cl2. Then the mixture was stirred for 24 hrs at room temperature, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with methanol/chloroform (1:10) solvent mixture as an eluant to give 108 mg of the title compound (d) (yield: 90%).

Workup

  1. additionwas added to the catalyst solution
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resultant was purified by Silica gel column chromatography with methanol/chloroform (1:10) solvent mixture as an eluant

Sources & evidence

ORD record
ord-976046ffdcb14d84bd71b690132bc09f
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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