Dimethylformamide → HCID 12136435, compound

Participants

Reaction Steps

To a suspension of (S)-2-(2-hydroxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.200 g, 0.774 mmol) in 1 mL of dioxane was added HCl (2.0 mL, 4 M in dioxane), and the resulting cloudy mixture was stirred at room temperature for 4 h. Concentration of the mixture was followed by addition of CH2Cl2. This process was repeated twice and final pumping under high vacuum for 12 h afforded the deprotected amine HCl salt as a white oil. This crude amine HCl salt was dissolved in 3 mL of DMF and treated with triethylamine (0.212 mL, 1.52 mmol). After stirring at room temperature for 10 min, a solution of (R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl chloride (Example 2) (0.211 g, 0.380 mmol) in 4 mL of CH2Cl2 was added rapidly dropwise via cannula. The reaction mixture was stirred at room temperature for 2 h. Following the addition of 75 mL of EtOAc, the organic layer was washed with three portions of water, then brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative TLC to afford 0.218 g (85%) of the title compound as a white foam (676.1, M+1).

Provenance & Evidence