反应详情

To a solution of 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetic acid (I52) (460 mg, 1.38 mmol) in THF (20 ml), were added DCC (341 mg, 1.65 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (223 mg, 1.65 mmol), and (R)-quinuclidin-3-ol (210 mg, 1.65 mmol). The resulting reaction mixture was stirred at room temperature for 15 hours, and then the solvent was evaporated. DCM is added, the insoluble was filtered off and the organic phase was washed twice with Na2CO3 and brine, dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography (DCM/MeOH=95/5 to 97/3), recovering first diastereomer 1 of C53 (71 mg, 12% yield), then a mixture of diastereomers of C53 (84 mg, 14% yield) and finally diastereomer 2 of C53 (21 mg, 4% yield).

1. customThe resulting reaction mixture
2. customthe solvent was evaporated
3. additionDCM is added
4. filtrationthe insoluble was filtered off
5. washthe organic phase was washed twice with Na2CO3 and brine
6. dry with materialdried over Na2SO4
7. customevaporated
8. customThe crude product was purified by flash chromatography (DCM/MeOH=95/5 to 97/3)
9. customrecovering first diastereomer 1 of C53 (71 mg, 12% yield)
10. additiona mixture of diastereomers of C53 (84 mg, 14% yield) and finally diastereomer 2 of C53 (21 mg, 4% yield)