1,2-Dichloroethane → [(2r)-3-{2-[2-Chloro-5-fluoro-6-(3-hydroxy-3-methyl-1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

Participants

Reaction Steps

(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.122 g, 0.4 mmol), racemic 1-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-3-methyl-3-pyrrolidinol (0.104 g, 0.4 mmol), NMM (0.13 mL, 1.2 mmol), HOAt (0.054 g, 0.4 mmol), EDC (0.077 g, 0.4 mmol) and DMF (2 mL) were combined. When the reaction was complete, the mixture was purified by RP-HPLC to provide [(2R)-3-{2-[2-chloro-5-fluoro-6-(3-hydroxy-3-methyl-1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide as a mixture of diastereomers (0.035 g, 16%). LCMS: (M+H)+=549.5.

Provenance & Evidence