Hydrochloric Acid → (R)-4-(1-Cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-ureidobutanoic acid

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Reaction Steps

(R)-2-Amino-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)butanoic acid (21 mg, 0.04 mmol) in CH2Cl2 (1.5 mL) was cooled to 0° C. To the solution were added triethylamine (0.05 mL, 0.32 mmol) and (trimethylsilyl)isocyanate (0.02 mL, 0.16 mmol). After stirring for 16 hours at room temperature, H2O (15 mL) and EtOAc (15 mL) were added. To the stirred mixture was added 1 N hydrochloric acid (1 mL). The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-20% MeOH/CH2Cl2 with 0.5% formic acid) to give the title compound in 5 mg. MS: (−) m/z 448.29 (M−1).

Provenance & Evidence