Water → Ethyl 2-methyl-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}-3-[4-(trifluoromethyl)phenyl]propanoate

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Reaction Steps

2.52 g (4.71 mmol) of the compound from Example 27A were dissolved in 70 ml of dichloromethane, and 14.5 ml (188.56 mmol) of trifluoroacetic acid were added. After stirring at RT for 3 h, the reaction solution was mixed with water, the phases were separated, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and dried over sodium sulfate, the solid was filtered off and the solvents were removed in vacuo. Purification of the crude product by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) and preparative HPLC (mobile phase: acetonitrile-water gradient) resulted in 1.01 g (48% of theory) of the title compound as mixture of diasteromers.

Provenance & Evidence