Triethylsilane → HCID 69556698, compound

Participants

Reaction Steps

0.837 g of the above prepared (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-(4-{2-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-propionyl]-oxazolidin-2-one (1.23 mmol) was dissolved in 3.2 ml of trifluoroacetic acid, treated at 0° with 0.977 ml of triethylsilane (5 eq.) and then kept for 16 h at ambient temperature, when TLC indicated the disappearance of starting material. The reaction mixture was then 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 0.702 g of the title compound as white foam.

Provenance & Evidence