反应详情

A solution of 7-[(phenoxyacetyl)amino]-8-oxo-3-(diethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester (618 mg, 1 mmol) in methylene chloride (20 mL) was cooled to 0° C. under nitrogen. Bromotrimethylsilane (612 mg, 4 mmol) was added and the stirred reaction warmed to room temperature. After two hours, the solvent was removed in vacuo. The residue was stirred at room temperature with methanol-water for 0.5 hours. The reaction product was concentrated and (1 mmol) of the product was treated with trifluoroacetic acid (10 mL) and triethylsilane (4 mL) and stirred vigorously for one hour. The volatiles were removed in vacuo and the residue purified by flash chromatography on silica gel (21/7/7/9 ethyl acetate/acetonitrile/acetic/acid/water) followed by medium pressure liquid chromatography on a C18 column eluted with 10% to 20% acetonitrile/water. The fractions containing pure product were combined and lyophilized to yield 20 mg (5%) 7-[(phenoxyacetyl)amino]-8-oxo-3-phosphinyl-1-azabicyclo[ 4.2.0]-oct-2-ene-2-carboxylic acid:

1. customthe stirred reaction
2. customthe solvent was removed in vacuo
3. concentrationThe reaction product was concentrated
4. stirringstirred vigorously for one hour
5. customThe volatiles were removed in vacuo
6. customthe residue purified by flash chromatography on silica gel (21/7/7/9 ethyl acetate/acetonitrile/acetic/acid/water)
7. washeluted with 10% to 20% acetonitrile/water
8. additionThe fractions containing pure product