反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 75 °C
PROCEDURE
实验过程
(S)-tert-Butyl 2-((S)-1-cyano-2-(4-iodophenyl)ethylcarbamoyl)piperidine-1-carboxylate (0.15 g) and bis[1,2-bis(diphenylphosphino)ethane]palladium (0) (2.80 mg, 3.10 μmol) were added to dioxane (3 mL) and 4-(N-(2-(tert-butyldimethylsilyloxy)ethyl)sulfamoyl)-phenylboronic acid (0.167 g) was added to the mixture which was then stirred, under nitrogen, for 10 min. Potassium carbonate (2M solution) (0.310 mL) was added and the reaction mixture was heated at 75° C. for 3 h. The reaction mixture was poured onto a Isolute HM-N cartridge and product was eluted with DCM. Solvent was removed in vacuo and the residue was dissolved in THF (5 mL). The resulting solution was cooled in an ice-bath and TBAF (1M solution in THF, 0.626 mL) was added and stirring was continued for 2 h. The reaction mixture was concentrated in vacuo and dissolved in formic acid (5 mL). The resulting solution was heated at 50° C. for 10 min. The reaction mixture was concentrated in vacuo, dissolved in methanol and loaded onto an SCX cartridge. Non-basic impurities were washed off with methanol then the desired compound was eluted with 10% ammonia in methanol. Solvent was removed in vacuo to give the title compound (0.025 g).
WORKUP
后处理
- additionwas added to the mixture which
- additionThe reaction mixture was poured onto a Isolute HM-N cartridge and product
- washwas eluted with DCM
- customSolvent was removed in vacuo
- dissolutionthe residue was dissolved in THF (5 mL)
- temperatureThe resulting solution was cooled in an ice-bath
- additionTBAF (1M solution in THF, 0.626 mL) was added
- stirringstirring
- waitwas continued for 2 h
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutiondissolved in formic acid (5 mL)
- temperatureThe resulting solution was heated at 50° C. for 10 min
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutiondissolved in methanol
- washNon-basic impurities were washed off with methanol
- washthe desired compound was eluted with 10% ammonia in methanol
- customSolvent was removed in vacuo