Water → HCID 59170803, compound

HRID 2247495Notes

Reaction equation

HRID 2247495 reaction equation
[CH2:1]1COCC1.[CH2:6]([CH:13]([NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]2)=[C:23]([O:33][CH3:34])[CH:22]=1)[C:14](=[O:16])[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[Mg]Cl.O>C(OCC)(=O)C>[CH2:6]([CH:13]([NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]2)=[C:23]([O:33][CH3:34])[CH:22]=1)[C:14]([OH:16])([CH3:1])[CH3:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 59170797HCID 59170797, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 59170803HCID 59170803, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a THF (1.0 mL) solution of (E)-N-(1-benzyl-2-oxopropyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide (12.0 mg), methyl magnesium chloride (3MTHF solution, 198 μL) was added at −78° C., the reaction solution was allowed to be warmed to room temperature and agitated for further 1 hour. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate ethanol=10:1), and 6.8 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate ethanol=10:1)

Sources & evidence

ORD record
ord-de2f4690145d4e749d8650eeea935bb5
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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