Trifluoroacetic acid → HCID 53246384, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(2-methyl-3-(2-(morpholinosulfonyl)benzyl)-5-phenyl-1H-pyrrol-1-yl)acetate (0.259 g, 0.537 mmol) (mixture of regioisomers—1.5:1.0) was dissolved in DCM (5.37 ml) and cooled to 0° C. DMAP (0.262 g, 2.147 mmol) was then added to the reaction in one portion, followed by TFA (0.758 ml, 5.37 mmol) in a drop-wise fashion. The ice bath was removed and the reaction was warmed to rt then refluxed for 16 h. At this time, the reaction was quenched with 1N HCl, and then diluted with 50 mL DCM. The layers were separated and the aqueous portion was then back-extracted with DCM (50 mL). The organics were combined, dried, filtered, and concentrated. The crude material ethyl 2-(2-methyl-3-(2-(morpholinosulfonyl)benzyl)-5-phenyl-4-(2,2,2-trifluoroacetyl)-1H-pyrrol-1-yl)acetate was then purified by silica gel chromatography using a 0-70% EtOAc/hexane gradient to furnish the desired material in 67% yield.

Provenance & Evidence