反应 #49994

反应方程式

(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

溶剂

ethyl acetate

dimethylsulfoxide

反应条件

后处理

1. 1
   workup.STIRRINGby stirring for 0.5 hour
2. 2
   其他An insoluble material was removed by filtration over celite
3. 3
   洗涤washed 3 times with ethyl acetate (20 ml)
4. 4
   其他the aqueous layer was separated from the organic layer
5. 5
   萃取extracted with ethyl acetate (200 ml)
6. 6
   洗涤washed with brine
7. 7
   干燥dried over anhydrous sodium sulfate
8. 8
   过滤After filtration
9. 9
   浓缩the filtrate was concentrated in vacuo
10. 10
    其他the concentrate was crystallized from a mixture of toluene and n-hexane (1:1)

实验过程

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.

来源