反应详情

温度

70 °C

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-(tert-butoxy)acetate (30 mg, 0.061 mmol) in Methanol (0.500 mL), Tetrahydrofuran (THF) (0.500 mL) and Water (0.500 mL) was treated with NaOH (54.7 mg, 1.368 mmol) and heated to 70° C. for 3 hours. The mixture was cooled to 0° C., treated with HCl (1M) until pH<2 and extracted with Ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min) to afford 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid (21.5 mg, 0.044 mmol, 73% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) ppm 13.33 (s, 1H) 7.58-7.69 (m, 2H) 7.42-7.54 (m, 3H) 7.23-7.38 (m, 4H) 5.89-5.95 (m, 1H) 5.74-5.81 (m, 1H) 5.07-5.15 (m, 1H) 3.50-3.59 (m, 3H) 0.88 (s, 9H); LCMS (m/z) ES+=479 (M+1).

1. temperatureThe mixture was cooled to 0° C.
2. extractionextracted with Ethyl acetate
3. washThe combined extracts were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min)