Hydrochloric Acid → p-Nitrobenzyl alpha-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetate

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Reaction Steps

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (218 mg) in methanol free methylene chloride (2.1 ml) is added aluminum chloride (220 mg) under ice cooling, and the mixture is stirred under argon atmosphere. After 35 minutes, the reaction mixture is poured into ice water containing 4 N-hydrochloric acid (4 ml), stirred for 10 minutes, and is extracted with chloroform. The extract solution is washed with water, dried and evaporated to give p-nitrobenzyl α-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (150 mg). Yellow foam. Yield: 94.6%. IR: νmaxCHCl3 3400, 1780, 1692, 1610, 1603 cm-1. NMR: δCDCl3 2.25d(10 Hz)1H, 4.25d(2 Hz)2H, 4.58s2H, 5.20-5.37m4H, 6.84-8.24m9H, 12.1s1H.

Provenance & Evidence