反应详情

5′-((1R,2R)-1-benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-2′-fluoro-biphenyl-2-carboxylic acid t-butyl ester (100 mg, 192 μmol, 1.0 eq.) was combined with 1:1 TFA/DCM (1 mL each) and stirred for 1 hour. The solvent was evaporated and THF (3 mL) and 1 M aqueous NaOH (577 μL, 3.0 eq.) were added. The mixture was stirred for 2 hours and EtOAc was added. The aqueous was extracted and the organic was washed with NaOH (0.2 mL), stirred, and the aqueous was extracted. The aqueous were acidified to pH ˜5 with concentrated HCl to yield a gummy solid. The aqueous was removed and the gummy solid was dissolved in AcOH and purified by preparative HPLC to yield the title compound (11.6 mg, 99% purity). MS m/z [M+H]+ calc'd for C26H24FNO6, 466.16. found 466.2.

1. customThe solvent was evaporated
2. stirringThe mixture was stirred for 2 hours
3. extractionThe aqueous was extracted
4. washthe organic was washed with NaOH (0.2 mL)
5. stirringstirred
6. extractionthe aqueous was extracted
7. customto yield a gummy solid
8. customThe aqueous was removed
9. dissolutionthe gummy solid was dissolved in AcOH
10. custompurified by preparative HPLC