Triethylamine → 4-nitrobenzyl 2-diazo-4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxo-azetidin-2-yl]-3-oxobutanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidine-2-yl]-3-oxobutanoate (61.2 mg) in acetonitrile (1.22 ml) was added a solution of p-toluenesulfonyl azide (38.3 mg) in acetonitrile (0.345 ml) at 0° C. After stirring for 10 minutes at 0° C., a solution of triethylamine (81.3 μl) in acetonitrile (0.732 ml) was added dropwise at 0° C. After the resultant solution was stirred for 30 minutes at 0° C., the solvent was distilled off, and the residue was flash-chromatographed on silica gel (0.9 g) eluting with a mixture of methylene chloride and ethyl acetate (40:1 to 3:1) to give 4-nitrobenzyl 2-diazo-4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]-3-oxobutanoate (56.5 mg) as an amorphous solid.

Provenance & Evidence