Formic Acid → HCID 21269030, compound

Participants

Reaction Steps

617 mg (2.39 mmol) of rac-(αS*,3S*,4R*)-4-[(p-chlorophenyl)thio-3-(1-hydroxyethyl)-2-azetidinone in 30 ml of tetrahydrofuran are treated with 1.25 g (4.8 mmol) of triphenylphosphine and 0.18 ml (4.8 mmol) of formic acid. A solution of 1.1 g (4.8 mmol) of diethyl azodicarboxylate in 10 ml of tetrahydrofuran is slowly added dropwise thereto, the reaction mixture is stirred at room temperature for 2 hours, evaporated and the residue is filtered through silica gel (hexane/ethyl acetate). The oil obtained (680 mg) is dissolved in 30 ml of methanol, the solution is treated with 3 drops of concentrated hydrochloric acid, left to stand at room temperature for 2 hours and evaporated. The residue is filtered through silica gel (hexane/ethyl acetate). There is obtained rac--(αR*,3S*,4R*)-4-[(p-chlorophenyl)thio]-3-(1-hydroxyethyl)-2-azetidinone of melting point 130° ; IR 1760 cm-1.

Provenance & Evidence