Water → HCID 86749007, compound

Participants

Reaction Steps

A solution of 1 g of N-(carboxymethylcarbonyl)paratoluenesulphonamide in 30 ml of acetonitrile is added, at room temperature and under stirring, with 0.97 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 1.56 g of (-)-N'-[pyrrolidin-2-yl)carbonyl]-N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-4-yl]piperazine, in this succession. After 3 hours the reaction mixture is added with 70 ml of water and extracted with ethyl acetate (3×20 ml). The combined organic extracts are washed with water (3×10 ml), dried over sodium sulfate and solvent is evaporated off under reduced pressure. The residue (1.5 g) is purified by silica gel chromatography (eluent 9.5:0.5 AcOEt/MeOH), to obtain 0.95 g of (-)-N'-[(1-(paratoluenesulphonamidocarbonyl-methylcarbonyl)pyrrolidin-2-yl)carbonyl]-N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-2-yl]piperazine, m.p. 170° C., [α]D =-26.9° (c=2.06 in EtOH).

Provenance & Evidence