Anisole → HCID 10923331, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.55 g (2 moles) of (3S,4S)-4-acetoxy-3-benzyl oxycarbonylamino-azetidin-2-one in 2 ml of anisole 0.40 g (3 mmoles) of anhydrous aluminum chloride are added at 20° C., by controlling the reaction by TLC (eluent: ethyl acetate/methanol=95/5 v/v). When the reaction is over, the mixture is filtered off and the filtered solution is concentrated under vacuum to obtain a residue of 0.260 g consisting of crude (3S,4S)-4-acetoxy-3-amino-azetidin-2-one. The residue is taken up with 30 ml of ethyl acetate and to the resulting solution 0.31 g (3 moles) of triethylamine and, afterwards, 0.695 g (4.5 mmoles) of phenylacetyl chloride are added. The mixture is stirred for 6 hours at 20°÷25° C., then it is concentrated under vacuum to obtain a residue which is taken up with ethyl acetate and subjected to a purification on a silica gel column (eluent: ethyl acetate). Thus, 0.165 g of (3S,4S)-4-acetoxy-3-phenylacetamido-azetidin-2-one (II) is obtained.

Provenance & Evidence