Acetamide → HCID 22013904, compound

HRID 1532734Notes

Reaction equation

HRID 1532734 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]([CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:8].[C:35]([NH2:38])(=[O:37])[CH3:36]>O>[C:35]([NH:38][C:10]([CH:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:18][CH:19]=1)[C:7]([O:6][CH3:5])=[O:8])=[O:12])(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 178AcetamideHCID 24386Thionyl Chloride2×HCID 9866203HCID 9866203, compound

Product 1

HCID 22013904HCID 22013904, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (1.0 ml) was added to 2-methoxycarbonyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionic acid (2.63 g, 6.43 mmol) obtained in Example 1, and the mixture was stirred with heating at 60° C. for 1 hr. Excess thionyl chloride was evaporated under reduced pressure and acetamide (504 mg, 8.54 mmol) was added to the residue. The mixture was stirred with heating at 120° C. for 30 min. Tetrahydrofuran-ethyl acetate (1:1, 100 ml) and water (50 ml) were added to the reaction mixture for partition. The organic layer was washed with saturated brine (50 ml), dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=1:1) to give the title compound (1.08 g, yield 34%) as a white solid.

Workup

  1. additionwas added to the residue
  2. stirringThe mixture was stirred
  3. temperaturewith heating at 120° C. for 30 min
  4. customfor partition
  5. washThe organic layer was washed with saturated brine (50 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-93050bdfa59d4fd8a3287ecaebb1e1b1
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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