Potassium cyanate → HCID 19965638, compound

HRID 977236Notes

Reaction equation

HRID 977236 reaction equation
C(O[C:4](=[O:31])[CH:5]([OH:30])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:29])[CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)C.[O-:32][C:33]#[N:34].[K+]>C(O)CCC>[CH3:22][C:21]1[O:20][C:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:18][C:17]=1[CH2:16][CH2:15][C:14]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH:5]2[O:30][C:33](=[O:32])[NH:34][C:4]2=[O:31])=[CH:9][CH:10]=1)=[O:29]

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 53877450HCID 53877450, compound

Product 1

HCID 19965638HCID 19965638, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-hydroxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyric acid ethyl ester (1.43 g), powdered potassium cyanate (0.83 g) and butanol (30 ml) was heated under refluxing conditions for 2 days. After the solvent was distilled off under reduced pressure, the residue was acidified with 2N hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated. The residue was purified by silica gel column chromatography. From the fraction eluted with chloroform-methanol (100:2), 5-[2-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]ethyl]-2,4-oxazolidinedione (0.56 g, 39%) was obtained, which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 173°-174° C.

Workup

  1. temperaturewas heated under refluxing conditions for 2 days
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washFrom the fraction eluted with chloroform-methanol (100:2)

Sources & evidence

ORD record
ord-3a7a54530e304c2fb485e12c5254d2fd
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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