(Z)-Methyl 2-(benzyloxycarbonylamino)-3-(3-(tert-butoxycarbonyl amino)-6-phenylpyridin-2-yl)acrylate → Methyl 2-(benzyloxycarbonylamino)-3-(3-(tert-butoxycarbonyl amino)-6-phenylpyridin-2-yl)propanoate

Participants

Reaction Steps

A suspension of 1F (650 mg, 1.29 mmol) and 5 wt % platinum on activated carbon (500 mg) in THF (60 mL) and MeOH (60 mL) was stirred at RT under H2 at 80 psi for 5 days. The reaction mixture was filtered through a Celite pad and the filtrate was concentrated. The residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as a foam (110 mg, 17%). LC/MS (method A): retention time=3.82 min, (M+H)+=506.

Provenance & Evidence