[(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 → HCID 58000615, compound

Participants

Reaction Steps

To a solution of [(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 (0.1737 g, 0.294 mmol) in MeOH (10 mL) was added 5% Rh/C (175 mg). The mixture was hydrogenated at 50 psi overnight, and was then filtered through a 0.2 μM membrane and concentrated in vacuo. To a solution of the residue in MeOH (4 mL) was added 20% Pd(OH)2/C (50% water, 5 mg). The mixture was hydrogenated under balloon pressure for 50 min. The mixture was then filtered though a 0.2 μM membrane, and the solution was concentrated in vacuo. The residue was purified by Gilson RPLC to give [(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (0.0670 g, 46% yield, mixture of diastereomers) as a while solid following crystallization from EtOAc-hexanes. LCMS: (M+H)+: 500.3.

Provenance & Evidence