Ethylmorpholine → N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(1-methylethyl)-5-oxoprolinamide

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Reaction Steps

1-(1-Methylethyl)-5-oxoproline (0.100 g, 0.58 mmol) was dissolved in dichloromethane (20 ml) and to this was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.111 g, 0.58 mmol), 1-Hydroxybenzotriazole (0.078 g, 0.58 mmol), and N-ethyl morpholine (0.223 ml, 1.75 mmol). Finally {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine was added to the mixture and stirring continued for ˜48 hrs. The mixture was then treated with saturated aqueous sodium hydrogen carbonate (20 ml) and stirred vigorously. The aqueous layer was removed using a phase separator and then the solvent was removed from the organic layer using an argon blow-down unit. The resulting residue was treated with a mixture of water and ethylacetate (25 ml, 1:1) and the aqueous layer was subsequently discarded. The organic layer was filtered through a phase separator and evaporated to give an oil. This was triturated with diethyl ether to give a solid and this was subsequently purified by mass-directed automated HPLC to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(1-methylethyl)-5-oxoprolinamide (0.097 g) as a white solid. LC/MS [M+H]+=363, retention time=2.48 minutes.

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