反应详情

温度

-78 °C

In an oven-dried 2 dram vial under N2, added (R)-tert-butyl 3-(2-(1-(6-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-5-fluoro-2-oxobenzo[d]oxazol-3(2H)-yl)ethyl)phenyl)-3-hydroxyazetidine-1-carboxylate (32-3, 55.8 mg, 0.075 mmol) to DCM (376 μl) and cooled to −78° C. Added DAST (19.88 μl, 0.150 mmol) dropwise. After 30 min at −78° C., removed from bath and allowed to slowly warm to RT. After 20 min, LCMS showed complete consumption of SM to desired product. Cooled reaction to 0° C., slowly quenched with 3 mL H2O. Diluted with 5 mL DCM, separated layers, back-extracted aqueous with 1×5 mL DCM. Washed combined organics with 1×5 mL H2O, 1×5 mL brine. Dried combined organics over Na2SO4, filtered, concentrated to give 32-5 as a white solid. Carried crude material forward to subsequent step.

1. customremoved from bath
2. temperatureto slowly warm to RT
3. waitAfter 20 min
4. customconsumption of SM to desired product
5. temperatureCooled
6. customreaction to 0° C.
7. customslowly quenched with 3 mL H2O
8. additionDiluted with 5 mL DCM
9. customseparated layers
10. extractionback-extracted aqueous with 1×5 mL DCM
11. washWashed
12. customDried
13. filtrationfiltered
14. concentrationconcentrated