Water → HCID 68710870, compound

HRID 2097562Notes

Reaction equation

HRID 2097562 reaction equation
[C:1](=O)([O-])O.[Na+].CI.[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([C:20]2[S:21][CH:22]=[C:23]([CH2:25][CH2:26][C:27]([C:29]3[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=3[C:31]([OH:33])=[O:32])=[O:28])[N:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[CH3:9].O>CN(C=O)C.C(OCC)(=O)C>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([C:20]2[S:21][CH:22]=[C:23]([CH2:25][CH2:26][C:27]([C:29]3[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=3[C:31]([O:33][CH3:1])=[O:32])=[O:28])[N:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 68708593HCID 68708593, compound

Product 1

HCID 68710870HCID 68710870, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydrogencarbonate (79 mg, 0.94 mmol) and methyl iodide (0.04 ml, 0.56 mmol) were added to a solution (4 ml) of 2-{3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionyl}benzoic acid (200 mg, 0.47 mmol) in DMF, followed by stirring at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with a saturated salt solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3). The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol, to thereby obtain 190 mg (yield: 92%) of methyl 2-{3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionyl}benzoate as colorless needles.

Workup

  1. washThe organic layer was washed with a saturated salt solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7f168e224e254f6ab00eaa711cc326e0
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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