Nitric Acid → HCID 178473867, compound

Participants

Reaction Steps

(2S,4R)-1-Acetyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-(2-benzothiazolylcarbonyl)butyl]-4-hydroxy-2-pyrrolidinecarboxamide as a free base in a diastereomeric ratio of 40:60 (591 mg, 1.27 mmol) was dissolved into a mixture of acetonitrile (6 mL) and ethanol (8 mL). To the mixture was added a solution of nitric acid (113 mg, 1.27 mmol) in acetonitrile (2 mL). Additional acetonitrile was then added until the cloud point. To the mixture were then added seeds of the desired nitrate salt. (The seeds were prepared by reacting chromatographed single diastereomer of the corresponding TFA salt with nitric acid, as described in Example 10). The mixture was then stirred for 18 hours at ambient temperature. The solid was filtered, washed with acetonitrile and dried in a vacuum oven to yield the title compound as an off-white solid.

Provenance & Evidence