Sodium Hydroxide → HCID 59900557, compound

Participants

Reaction Steps

A mixture of benzyl 2-[3-[(3-{(1R/S)-1-[(tert-butoxycarbonyl)amino]-2-methoxyethyl}phenethyl)amino]-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate (preparation 122) (248 mg, 0.42 mmol), ammonium formate (265 mg, 4.2 mmol) and 10% palladium on charcoal (100 mg) in methanol (10 ml) was heated under reflux for 25 hrs. The cooled reaction was filtered through Arbocel®, and NaOH (420 ml, 10M, 4.2 mmol) was added to the filtrate. This mixture was evaporated under reduced pressure, triturated and filtered with a dichloromethane:methanol (91:9) solution (3×), and the combined filtrates evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (100:0 to 93:7) to give the title compound as an oil, (35 mg, 18%).

Provenance & Evidence