(2S)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Boc Arg(NO2)OH (5.0 g, 15.6 mmol) was dissolved in 60 ml of tetrahydrofuran (THF) and was allowed to react with isobutyl chloroformate (2.06 ml, 15.6 mmol) in the presence of N-methylmorpholine (1.72 ml, 15.6 mmol) for 10 min at -20° C. The mixed anhydride preparation was filtered, and the filtrate was added to 120 ml of ethereal diazomethane. After stirring the reaction solution for 30 min at 0° C., 80 ml of ether was added. The product crystallized from the reaction solution in the cold. The Boc-Arg(HO2)CHNH2 product was dissolved in a minimum volume of THF and was allowed to react with ethanol HCl (20 mmol) at room temperature until nitrogen evolution ceased. was filtered the filtrate was added to 120 ml of ethereal diazomethane 80 ml of ether was added The product crystallized from the reaction solution in the cold The Boc-Arg(HO2)CHNH2 product was dissolved in a minimum volume of THF