1,2-Dichloroethane → [(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

Participants

Reaction Steps

To a solution of racemic 1-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N,2,2-tetramethyl-3-pyrrolidinamine pentahydrochloride (0.3649 g, 0.752 mmol) in DMF (5 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.2140 g, 0.701 mmol), N-methylmorpholine (0.770 mL, 7.00 mmol), 1-hydroxy-7-azabenzotriazole (114 mg, 0.838 mmol), and EDC (161 mg, 0.840 mmol). The solution was stirred overnight and purified directly by Gilson RPLC to provide [(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1755 g, 42% yield, mixture of diastereomers) as a brown oil. LCMS: (M+H)+: 590.4.

Provenance & Evidence