Hypodiphosphorous tetraiodide → 1,1-Dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

Participants

Reaction Steps

4.44 g of diphosphorus tetraiodide were suspended in 35 ml of pyridine, and after stirring for 5 minutes, 3.058 g of 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-2-hydroxy-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]octane-2-carboxylate were added all at once with stirring for 2 hours 40 minutes. The pyridine was distilled off and the residue was taken up in 50 ml of ethyl acetate. After filtering, 50 ml of N hydrochloric acid were added to the filtrate with vigorous stirring and the decanted organic phase was washed with water, dried and concentrated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with a mixture of methylene chloride and ethyl acetate (85-15). The fractions of interest were concentrated to dryness and crystallized from methanol to obtain 703 mg of 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-methoxymethyl-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate

Provenance & Evidence