(2R, 4E)-N-{(1S)-1-[(benzyloxy)carbonyl]-2,2-dimethylpropyl}-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pent-4-enamide → (2R)-N-[(1S)-1-(carboxy)-2,2-dimethylpropyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pentanamide

Participants

Reaction Steps

A solution of (2R, 4E)-N-{(1S)-1-[(benzyloxy)carbonyl]-2,2-dimethylpropyl}-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3′-methoxy-2-methylbiphen-4-yl)propyl]pent-4-enamide (534 mg, 0.87 mmol) in ethanol (75 mL) was hydrogenated over 10% palladium on charcoal (50 mg) at 3 bar and 20° C. for 5.75 h. The mixture was filtered through Arbocel filter aid, concentrated under reduced pressure and azeotroped with ethyl acetate to give (2R)-N-[(1s)-1-(carboxy)-2,2-dimethylpropyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3′-methoxy-2-methylbiphen-4-yl)propyl]pentanamide (384 mg, 61%), as a white solid, which was used for Examples 30 and 31 without purification.

Provenance & Evidence