Diethanolamine → SR 2555

Participants

Reaction Steps

A mixture of 4.00 g (21.6 mmol) of methyl 2-nitroimidazole-1-acetate and 4.0 g (38.0 mmol) of diethanolamine in 60.0 ml of methanol was stirred four days at room temperature. After removing the excess diethanolamine, the product was dissolved in 10 ml of methanol and chromatographed through a column of silica gel (70-230 mesh). Elution with 10% methanol in methylene chloride afforded 5.38 g (96%) of product as a hard gum that crystallized after several days to a cream colored hygroscopic solid on silica gel with 20% methanol in methylene chloride (Rf 0.47) and analyzed correctly for C9H14N4O5. The solubility of SR-2555 in 0.9% saline solution was over 300 mg/ml.

Provenance & Evidence