반응 #1265354

반응 방정식

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

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated in vacuo, water (20 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   추출the slurry was extracted with CH2Cl2 (3×100 mL)
4. 4
   세척the combined organic solutions were washed with saturated aq. NaHCO3 (20 mL) and brine (20 mL)
5. 5
   건조dried over anhydrous MgSO4
6. 6
   농축The solution was concentrated in vacuo
7. 7
   세척eluted with CH2Cl2:MeOH 100:1 to 10:1 (v/v)

실험 절차

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%).

출처