Reaktion #1265354

Reaktionsgleichung

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

Lösungsmittel

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle