Hydrogen Sulfide → HCID 86753666, compound

Participants

Reaction Steps

N-(N-4-Cyanobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid benzyl ester (0.6 g) was dissolved in pyridine (15 ml) and hydrogen sulfide gas was introduced for 1 hour. The reaction container was sealed and the reaction mixture was stirred at a room temperature for 12 hours. The solvent was distilled off and methyl iodide (2 g) was added, followed by refluxing in acetone for 3 hours. After the solvent and excess methyl iodide were distilled off from the reaction solution, ammonium acetate (0.2 g) was added and the mixture was refluxed in methanol for 6 hours. After the solvent was distilled off, the residue was dissolved in a small amount of methylene chloride and reprecipitated from hexane to yield N-(N-4-amidinobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid benzyl ester (0.25 g, 40.0%).

Provenance & Evidence