Ethyl Acetate → (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pentanamide

Participants

Reaction Steps

A solution of (2R, 5E)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pent-4-enamide (210 mg, 0.34 mmol) in ethanol:ethyl acetate=5:1 (10 mL) was hydrogenated over 10% palladium on charcoal (20 mg) at 3 bar and 20° C. for 3 h. The mixture was filtered through Arbocel filter aid and concentrated under reduced pressure to give (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-(3-fluoro-4-phenoxyphenyl)pentanamide (103 mg, 49%), as a colourless solid, which was used for Example 9 without purification.

Provenance & Evidence