Trifluoroacetic acid → methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate

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Reaction Steps

TFA (5 mL) was slowly added to a suspension of tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate (Intermediate 19, 3.55 g) in DCM (5 mL). The resultant dark solution was stirred at room temperature for 3 hours. The volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution. The layers were separated and the aqueous layer was extracted with more ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate (1.64 g) as a dark oil.

Provenance & Evidence