Triethylamine → 4-((2-Mercaptoethylthio)methyl)-4-methyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (1.85 g, 12.4 mmol) in DMF (5 ml) was added 1,2-ethanedithiol (10.0 ml, 119 mmol). Triethylamine (2.0 ml, 14 mmol) was added, and the solution heated to 90° C. for 2 h, then cooled to RT and concentrated in vacuo. Purification of the residue by flash chromatography (30%→80% EtOAc in hexanes) afforded a mixture of the title compound and various EDT disulfide adducts which was used without further purification. ESI/APCI expected for C7H13NO2S2: 207.04. Found: 208 (MH+), 300 (MH++EDT), 414 (MNa++2 EDT).

Provenance & Evidence