반응 #49994

반응 방정식

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

phosphoric acid

p-toluenesulfonic acid

water

→

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

용매

ethyl acetate

dimethylsulfoxide

반응 조건

후처리

1. 1
   workup.STIRRINGby stirring for 0.5 hour
2. 2
   기타An insoluble material was removed by filtration over celite
3. 3
   세척washed 3 times with ethyl acetate (20 ml)
4. 4
   기타the aqueous layer was separated from the organic layer
5. 5
   추출extracted with ethyl acetate (200 ml)
6. 6
   세척washed with brine
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   여과After filtration
9. 9
   농축the filtrate was concentrated in vacuo
10. 10
    기타the concentrate was crystallized from a mixture of toluene and n-hexane (1:1)

실험 절차

To a solution of (3S,4S)-4-(1-chloromethyl-ethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (20 g) in dimethylsulfoxide (160 ml), there were successively added water (40 ml), cuprous oxide (6.76 g) and p-toluenesulfonic acid (7.6 g), and the resultant mixture was warmed to 50° to 55° C. and stirred for 2 hours at the same temperature. After cooling down to room temperature, 1% aqueous phosphoric acid (90 ml) and ethyl acetate (200 ml) were poured into the reaction mixture, followed by stirring for 0.5 hour. An insoluble material was removed by filtration over celite and washed 3 times with ethyl acetate (20 ml). The filtrate and the washings were combined together, and the aqueous layer was separated from the organic layer and extracted with ethyl acetate (200 ml). The organic layer and the extract were combined together, washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, and the concentrate was crystallized from a mixture of toluene and n-hexane (1:1) to give crystals of (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone. m.p., 118°-120° C.

출처