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

Participants

Reaction Conditions

Reaction Steps

To a slurry of 60% of sodium hydride (110 mg, 2.76 mmol) in THF (8 mL) at 0° C. was added 1A (900 mg, 2.5 mmol) in several portions over 10 min. The reaction mixture was then brought to RT for 20 min, then cooled again at 0° C. A suspension of 1E (680 mg, 2.3 mmol) in THF (8 mL) was added over 10 min at 0° C., then the reaction was warmed up to RT. After stirring for 20 min, the reaction was quenched with water (30 mL). The aqueous layer was extracted with EtOAc (50 mL×2). The combined EtOAc extracts were dried (Na2SO4), filtered and concentrated. The resulting 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 an white foam (105 mg, 9%). LC/MS (method A): retention time=4.16 min, (M+H)+=504.

Provenance & Evidence