Trifluoroacetamide → HCID 86707844, compound

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A mixture of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-(1-oxo-hexahydro-1λ4-thiopyran-4-ylmethyl)-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (191 mg, 0.47 mmol), trifluoro-acetamide (104 mg, 0.92 mmol), (diacetoxyiodo)benzene (246 mg, 0.76 mmol), MgO (75 mg, 1.8 mmol) and rhodium acetate (10 mg, 0.023 mmol) in 10 ml of CH2Cl2 was stirred at room temperature for 2 h. Then, it was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography on silica gel. Yield: 80 mg of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-[1-oxo-1-(2,2,2-trifluoro-acetylimino)-hexahydro-1λ6-thiopyran-4-ylmethyl]-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (isomer A, compound P1.6) as a solid, mp 91-93° C. and 40 mg of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-[1-oxo-1-(2,2,2-trifluoro-acetylimino)-hexahydro-1λ6-thiopyran-4-ylmethyl]-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (isomer B, compound P1.7) as a solid, mp 87-89° C.

Provenance & Evidence