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

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Reaction Steps

To an ice-cold, stirring solution of benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (46 mg) in anhydrous DMF (1 ml) is added N-isopropyl-N,N-diethylamine (13 mg) and thiophenol (11 mg). The resulting solution is stirred in the cold for 15 mins. and at room temperature for 45 mins, then diluted with ethyl acetate (10 ml). The mixture is thoroughly washed with water (5×2 ml) and brine, dried with MgSO4, filtered, and evaporated to dryness. The residue is purified on a silica gel GF plate to yield benzyl 6-(1-hydroxyethyl)-3-phenylthio-1-azabicyclo[3.2.0]hept-b 2-en-7-one-2-carboxylate.

Provenance & Evidence