Hydrochloric Acid → HCID 13937969, compound

Participants

Reaction Steps

(Z)-[[[1-(2-Amino-4-thiazolyl)-2-oxo-2-[[2-oxo-1-(sulfooxy)-7-oxa-1-azaspiro[3.5]non-3-yl]-amino]ethylidene]amino]oxy]acetic acid diphenylmethyl ester, monopotassium salt (0.39 g, 0.57 mmole) was slurried in 6 ml of dry dichloromethane and 1.5 ml of anisole at -10° C. under argon and treated with 10 ml of trifluoroacetic acid. After 1 hour, dry toluene (12 ml) was added and the volatiles were removed in vacuo at 10° C. The residue was washed twice with hexane, then taken up in water and the pH adjusted to 6.75 with dilute potassium bicarbonate. Chromatography on HP-20 in water gave product mixed with inorganics. The impure product was lyophilized, taken up in water and the pH adjusted to 2.5 with dilute hydrogen chloride. Chromatography on HP-20 in a water-50% acetone:water gradient and lyophilization of the pure product fractions yielded the title compound as a white powder, 177 mg.

Provenance & Evidence