反应 #1265354

反应方程式

Sodium hydroxide

benzoyl chloroformate

compound 5

{2-[2-(2-{2-[2-(2-Amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-acetic acid tert-butyl ester

→

compound 6

{2-[2-(2-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-acetic Acid Tert-butyl Ester

溶剂

water

ethyl acetate

反应条件

后处理

1. 1
   浓缩The reaction mixture was concentrated in vacuo, water (20 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   萃取the slurry was extracted with CH2Cl2 (3×100 mL)
4. 4
   洗涤the combined organic solutions were washed with saturated aq. NaHCO3 (20 mL) and brine (20 mL)
5. 5
   干燥dried over anhydrous MgSO4
6. 6
   浓缩The solution was concentrated in vacuo
7. 7
   洗涤eluted with CH2Cl2:MeOH 100:1 to 10:1 (v/v)

实验过程

Sodium hydroxide (2.0 mL of a 3M in water, 6.0 mmol) and benzoyl chloroformate (0.52 mL, 0.36 mmol) were added in portions to compound 5 (0.90 g, 2.3 mmol) in ethyl acetate (10 mL) and the resulting mixture was stirred overnight. The reaction mixture was concentrated in vacuo, water (20 mL) was added, and the slurry was extracted with CH2Cl2 (3×100 mL), and the combined organic solutions were washed with saturated aq. NaHCO3 (20 mL) and brine (20 mL), and dried over anhydrous MgSO4. The solution was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (100 g) and eluted with CH2Cl2:MeOH 100:1 to 10:1 (v/v) to afford compound 6 as a colorless oil (0.93 g, 76%).

来源