反应详情

To a cold (0° C.) solution of (R)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)-4,4-dimethylpentanoic acid, 3a, (0.08 g, 0.14 mmol) in MeOH (2.6 mL) was added sodium methanolate (2.91 mL of 25% w/v, 13.46 mmol). The reaction was stirred at room temperature for 30 min and then quenched by dilution into aqueous saturated ammonium chloride solution. The MeOH was evaporated in vacuo and the resulting aqueous phase diluted with EtOAc, then extracted with EtOAc (3×). The organics were dried (Na2SO4), filtered and concentrated in vacuo. Recrystallization from MeOH provided 52 mg of the desired product 1 as a white powder: 1H NMR (d6-DMSO) δ 12.25 (s, 1H): 12.0 (bs, 1H): 8.8 (s, 1H): 8.3 (s, 1H): 8.25 (s, 1H); 8.1 (s, 1H): 7.45 (d, 1H); 4.75 (t, 1H); 2.5 (m, 2H), 1.0 (s, 9H); LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.06 minutes (M+H) 392.21.

1. customquenched by dilution into aqueous saturated ammonium chloride solution
2. customThe MeOH was evaporated in vacuo
3. additionthe resulting aqueous phase diluted with EtOAc
4. extractionextracted with EtOAc (3×)
5. dry with materialThe organics were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customRecrystallization from MeOH