p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-5-chloro-4,4-dimethyl-3-oxopentanoate → p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-4,4-dimethyl-5-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thio]-3-oxopentanoate

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Reaction Steps

A mixture of 118 mg (0.25 mmol) of p-nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-5-chloro-4,4-dimethyl-3-oxopentanoate and 82 mg (0.59 mmol) of the Na salt of 1-methyl-5-mercapto-1,2,3,4-tetrazole are stirred for 20 hours at room temperature in 0.2 ml of dimethylformamide. The reaction mixture is chromatographed directly on a chromatography column containing 6 g of silica gel using toluene:ethyl acetate (19:1), to give 60 mg of pure title compound as a non-crystalline solid.

Provenance & Evidence