Perchloric Acid → methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate

Participants

Reaction Steps

A solution of methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate (3.3 g, 4.53 mmol) in t-Butyl acetate (30 mL) was treated with perchloric acid (0.423 mL, 7.04 mmol) and the resultant was stirred at room temperature for 3 hours. The mixture was diluted with Ethyl acetate, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate (2.3 g, 4.67 mmol, 73% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.43-7.47 (m, 3H) 7.37-7.41 (m, 1H) 7.32-7.35 (m, 4H) 7.01-7.05 (m, 1H) 5.92-5.96 (m, 1H) 5.83-5.88 (m, 2H) 5.21-5.24 (m, 1H) 3.82 (s, 3H) 3.67 (s, 3H) 0.96 (s, 9H); LCMS (m/z) ES+=493 (M+1).

Provenance & Evidence