To a solution of (3S)-4-(5-fluoro-6-hydrazino-2-methyl-4-pyrimidinyl)-3-methyl morpholine dihydrochloride (251.5 mg, 0.752 mmol) in DMF (6 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid, N,N-diisopropylethylamine salt, isopropanol solvate (306.1 mg, 0.619 mmol), N-methylmorpholine (0.410 ml, 3.73 mmol), 1-hydroxy-7-azabenzotriazole (0.101 g, 0.742 mmol), and EDC (0.142 g, 0.741 mmol). The solution was allowed to stir overnight, and was then purified directly by Gilson RPLC to give [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(3S)-3-methyl-4-morpholinyl]-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (314.6 mg, 93%) as an orange foam. LCMS: (M+H)+: 549.2.
