反应详情

温度

15 °C

Potassium t-butoxide (618 mg, 5.5 mmol) was added to a stirred solution of BOC trans-4-hydroxyproline (424 mg, 1.83 mmol) in DMSO (10 mL) at RT. The reaction mixture was stirred for 30 minutes and cooled to 15° C., and the product from Step 3 (500 mg, 1.83 mmol) was added. The reaction mixture was stirred overnight and partitioned between ice-cold 10% citric acid and EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, and the solvent evaporated. The crude product was dissolved in EtOH (100 mL), cooled to 0° C. and HCl bubbled through until saturated. The reaction mixture was allowed to warm to RT and stirred for 24 hours. The volatiles were evaporated and the residue azeotroped with EtOH (4×) to give the title compound as a tan solid (555 mg). LRMS ESI+ (M+H)+ 395.0.

1. stirringThe reaction mixture was stirred overnight
2. custompartitioned between ice-cold 10% citric acid and EtOAc
3. washThe organic phase was washed with water and brine
4. dry with materialdried over Na2SO4
5. customthe solvent evaporated
6. dissolutionThe crude product was dissolved in EtOH (100 mL)
7. temperaturecooled to 0° C.
8. customHCl bubbled through until saturated
9. temperatureto warm to RT
10. stirringstirred for 24 hours
11. customThe volatiles were evaporated
12. customthe residue azeotroped with EtOH (4×)