HCID 178442250, compound → HCID 178448996, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence