Urea → 3-[4-(4-Methoxyphenyl)-5-phenyl-1,3-oxazol-2-yl]propanoic acid

HRID 2380160Notes

Reaction equation

HRID 2380160 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)O)=O)=[CH:13][CH:12]=1.COC1C=CC(C(C(C2C=CC=CC=2)O)=O)=CC=1.[NH2:45]C(N)=O>C(O)(=O)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:45]=[C:4]([CH2:3][CH2:2][C:1]([OH:8])=[O:7])[O:6][C:19]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 131717098HCID 131717098, compound

Product 1

HCID 189565763-[4-(4-Methoxyphenyl)-5-phenyl-1,3-oxazol-2-yl]propanoic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the crude 4-methoxybenzoin hemisuccinate (20.8 g, 0.061 mole) of Step B, urea (8.7 g, 0.146 mole) and acetic acid (60 mL) is heated at reflux under nitrogen for 5.5 hours. The mixture is cooled and poured into ice water. The liberated oil is extracted with ethyl acetate (3x). The extracts are washed with water until neutral and then extracted with saturated sodium carbonate. The combined aqueous extracts are carefully acidified in the cold with concentrated HCl and extracted with ethyl acetate. The organic extract is dried (MgSO4) and evaporated to dryness to provide a waxy yellow oil (19.6 g). Purification of the residue by flash chromatography (on silica Merck-60, eluant: dichloromethane-ethyl acetate 8:2) yields a pale yellow solid (14.3 g, 72.7%), m.p. 100°-101° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 5.5 hours
  3. temperatureThe mixture is cooled
  4. extractionThe liberated oil is extracted with ethyl acetate (3x)
  5. washThe extracts are washed with water until neutral and
  6. extractionthen extracted with saturated sodium carbonate
  7. extractionextracted with ethyl acetate
  8. extractionThe organic extract
  9. dry with materialis dried (MgSO4)
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-583b0b75ae0c4c97803d4581baaf284c
Source dataset
uspto-grants-1994_11
Patent number
US05364944

Reaction notes

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