Dichloromethane → HCID 59170797, compound

HRID 1446485Notes

Reaction equation

HRID 1446485 reaction equation
C(Cl)Cl.[CH2:4]([CH:11]([NH:15][C:16](=[O:33])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]2)=[C:21]([O:31][CH3:32])[CH:20]=1)[CH:12]([OH:14])[CH3:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:4]([CH:11]([NH:15][C:16](=[O:33])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]2)=[C:21]([O:31][CH3:32])[CH:20]=1)[C:12](=[O:14])[CH3:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 59170931HCID 59170931, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 59170797HCID 59170797, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride (2.0 mL) solution of (E)-N-(1-benzyl-2-hydroxy propyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide (29.0 mg), Dess-Martin reagent (60.7 mg) was added. After agitating the reaction solution at room temperature for 4 hours and 30 minutes, a saturated sodium bicarbonate 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 15.4 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-e48fe0b28a594f95a96c29a17553b317
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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