Hydrochloric Acid → HCID 9890862, compound

Participants

Reaction Steps

In 10 ml of methanol was dissolved 480 mg of (S)-4-(N-benzyloxycarbonylglycyl)-3-methoxycarbonylmethyl-2-oxo-piperazin-1-acetic acid t-butyl ester obtained in Working Example 58. To the solution was added 100 mg of 10% palladium-carbon, and the mixture was stirred for one hour at room temperature in a hydrogen streams. The catalyst was filtered off, and the filtrate was concentrated to give an oily product, which was dissolved in 5 ml of dimethylformamide. To the solution were added 200 mg of 4-amidinobenzoic acid hydrochloride, then 200 mg of (1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. The mixture was stirred for one hour at room temperature. The reaction mixture was diluted with ethyl acetate, washed with a 5% aqueous solution of potassium hydrogensulfate, then a 10% aqueous solution of sodium hydrogencarbonate, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure to leave an oily product. The oily product was dissolved in 5 ml of methylene chloride. To the solution was added 5 ml of trifluoroacetic acid, and the mixture was stirred for one hour at room temperature. The reaction mixture was concentrate to give a crude product, which was made into hydrochloride with 1N HCl, followed by purification by means of a C18 --ODS column to afford 250 mg of the title compound as colorless powder.

Provenance & Evidence