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

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (46 mg), 2-(N,N-dimethylamino)ethyl mercaptan hydrochloride (14.2 mg), and triethylamine (14 μl) in anhydrous DMF (2 ml) is stirred at room temperature (25° C.) for 2 hrs. The mixture is added to ethyl acetate (20 ml), washed with 5% sodium bicarbonate (10 ml), water (4×10 ml) and brine, dried over MgSO4, filtered, concentrated in vacuo. Purification of the residue by chromatography on silica gel gives benzyl 6-(1-hydroxyethyl)-3-(2-dimethylaminoethylthio)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Provenance & Evidence