3,5-Difluoroaniline → (S)-tert-Butyl 4-(benzyloxy)-1-(3-bromo-2-(3,5-difluorophenylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxobutan-2-ylcarbamate

Participants

Reaction Steps

(S)-Methyl 1-(4-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate (4 g, 7.84 mmol) was treated with 3,5-difluoroaniline (5.06 g, 39.19 mmol) and trimethyl aluminium (2 M in toluene, 19.6 mL, 39.18 mmol) according to the method of Preparation 10a. The residue was purified using SP1® Purification System (0% to 50% hexane-ethyl acetate) to obtain 2.18 g (41% yield) of the title compound as a white solid. Purity 88%.

Provenance & Evidence