反応 #49994

反応方程式

(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

溶媒

ethyl acetate

dimethylsulfoxide

反応条件

後処理

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

実験手順

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.

出典