반응 #96129

반응 방정식

diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-chloro-2-propen-2-yl)acetate

ozone

→

diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(2-chloro-1-hydroxyethylidene)acetate

용매

methylene chloride

methanol

반응 조건

후처리

1. 1
   기타Then excess ozone is purged with oxygen
2. 2
   workup.ADDITIONmixed with an aqueous solution of 95% sodium hydrogen sulfite (100 mg)
3. 3
   세척the solution is washed with 5% sodium hydrogen carbonate and water
4. 4
   기타dried
5. 5
   농축concentrated
6. 6
   기타to remove methylene chloride
7. 7
   기타The resultant oil (132 mg) is purified over thin-layer chromatographic plate (Merck 60F-254)
8. 8
   workup.ADDITIONa mixture of benzene and ethyl acetate (1:1)

실험 절차

To a dry ice acetone cooled solution of diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-chloro-2-propen-2-yl)acetate (160 mg) in a mixture of methylene chloride (3.2 ml) and methanol (0.3 ml) is introduced ozone until the reaction mixture shows blue color. Then excess ozone is purged with oxygen, mixed with an aqueous solution of 95% sodium hydrogen sulfite (100 mg), warmed to room temperature to decompose the ozonide. After 1.5 hours, the solution is washed with 5% sodium hydrogen carbonate and water, dried, and concentrated to remove methylene chloride. The resultant oil (132 mg) is purified over thin-layer chromatographic plate (Merck 60F-254) using a mixture of benzene and ethyl acetate (1:1) as developing solvent to give diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(2-chloro-1-hydroxyethylidene)acetate (44 mg) as glass.

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