Triethylamine → Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-(2-dimethylaminoethylthio)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Participants

Reaction Steps

A mixture of benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (51 mg), 2-(N,N-dimethylamino)ethylmercaptan hydrochloride (14.2 mg), and triethylamine (14 ml) in anhydrous DMF (2 ml) is stirred at room temperature for 2 hours. The mixture is diluted with ethyl acetate (20 ml), washed with 5% sodium bicarbonate (2×5 ml), water (4×10 ml), and brine, dried with MgSO4, filtered, and concentrated in vacuo. The residue is purified by chromatography on silica gel to yield benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-(2-dimethylaminoethylthio)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Provenance & Evidence