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

Participants

Reaction Steps

To a solution of (3S)-1-(5-fluoro-6-hydrazino-2-methyl-4-pyrimidinyl)-4,4-dimethyl-3-pyrrolidinol (0.125 g, 0.490 mmol) in DMF (3 mL) was added (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.1246 g, 0.408 mmol), N-methylmorpholine (0.225 ml, 2.046 mmol), 1-hydroxy-7-azabenzotriazole (67 mg, 0.492 mmol), and EDC (94 mg, 0.490 mmol). The mixture was stirred overnight and then purified directly by Gilson RPLC to give [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1606 g, 73% yield) as a purple oil. LCMS: (M+H)+: 543.3.

Provenance & Evidence