HCID 58784302, compound → HCID 58784301, compound

Participants

Reaction Steps

A solution of 6-(2-azido-ethoxymethyl)-4-(2-chloro-phenyl)-3-{3-[methyl-(3-phenyl-propionyl)-amino]-propyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (27 mg, 0.046 mmol) in EtOH (5 mL) was hydrogenated in the presence of 5% palladium on calcium carbonate poisoned with lead (10 mg). After 3 h, the catalyst was removed using a filter syringe. The filtrate was concentrated in vacuo to afford 29 mg of thick, colorless oil as crude product (87% pure by analytical HPLC). The crude product was purified by preparative HPLC (from 30% B to 100% B for 10 min, Solvent A=90% H2O-10% MeOH-0.1% TFA Solvent B=10% MeOH-90% H2O-0.1% TFA, at 20 mL/min using column YMC ODS S5 20×100 mm). The desired fractions were combined and concentrated to remove most of the MeOH. The concentrate was taken up in EtOAc (50 mL) and basicified with saturated aqueous NaHCO3 solution. The EtOAc extract was washed with brine, dried (Na2SO4), filtered, concentrated and dried in vacuo to afford 14.5 mg (43%) of purified material as a thick, colorless oil.

Provenance & Evidence