Water → HCID 178459504, compound

HRID 543238Notes

Reaction equation

HRID 543238 reaction equation
[C:1]([NH:9][CH:10]([CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(C)[CH:25]=CC(S(O)(=O)=O)=C[CH:21]=1.O>C1C=CC=CC=1.C(O)C#C>[C:1]([NH:9][CH:10]([CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)[C:11]([O:13][CH2:25][C:20]#[CH:21])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962Water3×HCID 6101p-Toluenesulfonic acidHCID 178523258HCID 178523258, compound

Product 1

HCID 178459504HCID 178459504, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 7859Propargyl alcoholSolvent

Procedure

5 gm of 2-(benzoylamino)-3-(imidazol-4-yl)propanoic acid in 100 ml of benzene, 5 ml of propargyl alcohol, and 5.22 gm of p-toluenesulfonic acid.H2O was heated at reflux with the azeotropic removal of water by means of a Dean-Stark apparatus. After approximately 2 days of refluxing and the stoichiometric amount of water was produced, the reaction mixture was cooled, and a precipitate, the p-toluenesulfonic acid salt of the title compound was filtered out. The salt was taken up in water, the pH adjusted to 7.5 with 1.0N NaOH in a two phase system of water-dichloromethane. The layers were separated and the aqueous portion extracted 3×30 ml of CH2Cl2. The organic fractions were pooled, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound.

Workup

  1. temperatureAfter approximately 2 days of refluxing
  2. temperaturethe reaction mixture was cooled
  3. filtrationa precipitate, the p-toluenesulfonic acid salt of the title compound was filtered out
  4. customThe layers were separated
  5. extractionthe aqueous portion extracted 3×30 ml of CH2Cl2
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-890fa966f624441891907011743913e5
Source dataset
uspto-grants-1987_04
Patent number
US04661510

Reaction notes

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