Triethylsilane → (S)-4-Benzyl-3-((2S)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one

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Reaction Steps

The above prepared (S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one (0.255 g, 0.42 mmol) was dissolved in 2.2 ml of trifluoroacetic acid, treated at 0° with 0.663 ml of triethylsilane (10 eq.) and then kept for 3 h at ambient temperature, when TLC indicated the disappearance of starting material. The reaction mixture was poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed with water and brine (pH of aq. phase˜8), dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) delivered 0.196 g of the title compound as colorless foam.

Provenance & Evidence