Réaction #49993

Équation de réaction

(3S,4S)-4-(1-Methylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

chlorine

Water

sodium thiosulfate

→

(3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Solvants

ethyl acetate

carbon tetrachloride

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGwas stirred for 0.5 hour
2. 2
   LavageThe organic layer was washed successively with a saturated sodium bicarbonate solution and brine
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   FiltrationAfter filtration
5. 5
   Concentrationthe filtrate was concentrated in vacuo

Mode opératoire

(3S,4S)-4-(1-Methylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (200 g) was dissolved in ethyl acetate (3 liters), and a solution of chlorine in carbon tetrachloride (3.85%, 870 g) was added dropwise thereto at room temperature over a period of 15 minutes, followed by stirring for 1 hour. Water (1 liter) and then 10% aqueous sodium thiosulfate solution (50 ml) were poured into the reaction mixture, which was stirred for 0.5 hour and allowed to stand. The organic layer was washed successively with a saturated sodium bicarbonate solution and brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo to give (3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone. m.p., 84°-85° C.

Source