反应详情

To a solution of (+/−)-tert-butyl ((1R,2R,3S,5R)-5-(3-((tert-butoxycarbonyl)amino)pyridin-4-yl)-2-hydroxy-3-methylcyclohexyl)carbamate (1.0 equiv.) in pyridine (0.17 M) was added MsCl (5.0 equiv.). The capped solution was stirred for 5 minutes and then the homogeneous solution was left standing at rt for 16 hrs. The volatiles were removed in vacuo and the residue was partitioned between EtOAc and H2O. The organic layer was washed with H2O, 10% CuSO4, H2O, Na2CO3(sat.), NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography to yield (+/−)-(1R,2R,4R,6S)-2-(tert-butoxycarbonylamino)-4-(3-(tert-butoxycarbonylamino)pyridin-4-yl)-6-methylcyclohexyl methanesulfonate in 59% yield. LC/MS (m/z)=500.3 (MH+), Rt=0.74 min.

1. waitthe homogeneous solution was left
2. waitstanding at rt for 16 hrs
3. customThe volatiles were removed in vacuo
4. customthe residue was partitioned between EtOAc and H2O
5. washThe organic layer was washed with H2O, 10% CuSO4, H2O, Na2CO3(sat.), NaCl(sat.)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified by ISCO SiO2 chromatography