HCID 178442250, compound → HCID 178448996, compound

HRID 543239Notes

Reaction equation

HRID 543239 reaction equation
C([NH:9][C:10]([CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1)([CH:14]=[C:15]=[CH2:16])[C:11]([OH:13])=[O:12])(=O)C1C=CC=CC=1>Cl.O>[NH2:9][C:10]([CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1)([CH:14]=[C:15]=[CH2:16])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 178442250HCID 178442250, compound

Product 1

HCID 178448996HCID 178448996, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2.0 g of 2-(benzoylamino)-2-(imidazol-4-ylmethyl)-penta-3,4-dienoic acid was taken in 20 ml of 20% HCl and heated at 80° C. for 48 hours. The solution was cooled, diluted with 20 ml of water and washed with methylene chloride 3×40 ml. The aqueous phase was adjusted to pH 7.0, cooled to 0° C. and an excess of sodium borohydride added. After two hours at 0° C., the pH was adjusted to 2.0 and the solution introduced onto an ion-exchange chromotography (BioRad Ag 50×8 column), and eluted with 0.3M ammonium acetate buffer pH 4.5-8.0. Fractions between pH 6.5-8.0 were pooled and desalted with 20% pyridine-water. Concentration of the pyridine-water fractions gave an oil which upon fractional crystallization gave the title compound.

Workup

  1. temperatureThe solution was cooled
  2. washwashed with methylene chloride 3×40 ml
  3. temperaturecooled to 0° C.
  4. additionan excess of sodium borohydride added
  5. additionthe solution introduced onto an ion-exchange chromotography (BioRad Ag 50×8 column)
  6. washeluted with 0.3M ammonium acetate buffer pH 4.5-8.0
  7. customConcentration of the pyridine-water fractions gave an oil which
  8. customupon fractional crystallization

Sources & evidence

ORD record
ord-de31c5364c974814ad5d690b241e2430
Source dataset
uspto-grants-1987_04
Patent number
US04661510

Reaction notes

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