Reaktion #215085

Reaktionsgleichung

butyl cis-1-benzhydryl-3-azido-4-oxo-2-azetidine carboxylate

potassium persulfate

disodium phosphate dodecahydrate

water

→

crude material

Ausbeute 175.5%

Butyl cis-3-azido-4-oxo-2-azetidinecarboxylate

Ausbeute 175.5%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas thoroughly degassed with argon
2. 2
   Temperaturheated to 80°-85° C. under argon for three hours
3. 3
   TemperaturThe reaction mixture was cooled
4. 4
   Sonstigethe acetonitrile removed on the rotary evaporator
5. 5
   Extraktionextracted three times with ethyl acetate
6. 6
   ExtraktionThe combined organic extractions
7. 7
   Waschenwere washed with brine
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuo

Vorschrift

A mixture of 200 mg (0.529 mmole) of butyl cis-1-benzhydryl-3-azido-4-oxo-2-azetidine carboxylate, 473 mg (1.75 mmole) of potassium persulfate, 307 mg (0.858 mmole) of disodium phosphate dodecahydrate, 9.2 ml of water and 8.4 ml of acetonitrile was thoroughly degassed with argon and then heated to 80°-85° C. under argon for three hours. The reaction mixture was cooled and the acetonitrile removed on the rotary evaporator. The aqueous residue was saturated with solid sodium chloride and extracted three times with ethyl acetate. The combined organic extractions were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 197 mg of crude material. This material was chromatographed on ten grams of 70-230 mesh silica gel and 31 mg (28%) of the desired product, a light yellow foam was eluted with 20% EtOAc in benzene. tlc: silica gel GF; 20% ethylacetate benzene, R.f.=0.15.

Quelle