Urea → HCID 22013878, compound

HRID 1532737Notes

Reaction equation

HRID 1532737 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:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:26][C:27]=2[CH2:28]C)=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:8].[NH2:36][C:37]([NH2:39])=[O:38].C(Cl)(Cl)Cl>O>[CH3:5][O:6][C:7]([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:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[O:26][C:27]=2[CH3:28])=[CH:18][CH:19]=1)[C:10]([NH:36][C:37]([NH2:39])=[O:38])=[O:12])=[O:8]

Participants

6

Reactant 4

HCID 1176UreaHCID 6212ChloroformHCID 24386Thionyl Chloride2×HCID 22013899HCID 22013899, compound

Product 1

HCID 22013878HCID 22013878, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (4.0 ml) was added to 2-methoxycarbonyl-3-[4-(2-(5-ethyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionic acid (4.10 g, 10.0 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 urea (900 mg, 15.0 mmol) was added to the residue obtained, which was followed by stirring with heating at 100° C. for 45 min. Chloroform (100 ml) and water (50 ml) were added 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 (3.71 g, yield 82%) as a white solid.

Workup

  1. additionwas added to the residue
  2. customobtained
  3. stirringby stirring
  4. temperaturewith heating at 100° C. for 45 min
  5. customfor partition
  6. washThe organic layer was washed with saturated brine (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3b704ba3fb684b4fb4f84a855aee406a
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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