Methyl iodide → 5-(S)-Azidomethyl-3-[4'-methylthio-3'-fluorophenyl]oxazolidine-2-one

Participants

Reaction Steps

5% TFA and 2.5% triisopropylsilane in DCM (4 ml) was added to 5-(S)-azidomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]oxazolidine-2-one (0.250 g, 0.490 mmol; prepared as described above for Example 6), and the mixture stirred for 1 h at r.t. Solvent was removed under vacuum and the residue dissolved in DMF (2 ml). Iodomethane (0.046 ml, 0.735 mmol) was added followed by dropwise addition of triethylamine (0.136 ml, 0.979 mmol). The mixture was stirred at r.t. for 2 h, evaporated, and the residue purified by PTLC (50% ethyl acetate in DCM) to give the product as a white solid (0.124 g, 90%). MS (m/z): [M+H]+=283.

Provenance & Evidence