Acetic Acid → HCID 86602477, compound

HRID 1446504Notes

Reaction equation

HRID 1446504 reaction equation
[CH2:1]([O:3][C:4](=[O:29])/[C:5](=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]2)=[C:17]([O:27][CH3:28])[CH:16]=1)/[CH2:6][CH2:7][CH2:8][CH:9]1OCC[O:10]1)[CH3:2].C(O)(=O)C.FC(F)(F)C(O)=O.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:29])/[C:5](=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]2)=[C:17]([O:27][CH3:28])[CH:16]=1)/[CH2:6][CH2:7][CH2:8][CH:9]=[O:10])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 66961085HCID 66961085, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 86602477HCID 86602477, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an aqueous solution (2.0 mL) of (E)-5-[1,3]dioxolan-2-yl-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl ester (480 mg), acetic acid (1.0 mL) and trifluoroacetic acid (1.0 mL) were added one by one, and the reaction solution was agitated at room temperature for 2.5 hours. A saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution after confirming disappearance of the starting materials, 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 400 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-26f782a5b5a84262a5a68c884d31eb42
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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