반응 #54859

반응 방정식

(1-pyrryl) acetic acid

3-[[(5 methyl - 1, 3, 4-thiadiazol-2-yl) thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

N, N'-dicyclohexylcarbodiimide

carbodiimide

sodium bicarbonate

→

7-[[(1-Pyrryl)acetyl]amino]-3-[[(5-methyl-1,3,4-thia-diazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

용매

dioxane

water

반응 조건

후처리

1. 1
   온도This solution is cooled in an ice bath and to it
2. 2
   여과temperature, the reaction mixture is filtered
3. 3
   기타to remove solids
4. 4
   기타The filtrate is evaporated to dryness
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축The ethyl acetate solution is concentrated
8. 8
   workup.ADDITIONtreated with hexane
9. 9
   기타The title compound precipitates from solution
10. 10
    여과is filtered
11. 11
    기타dried

실험 절차

(1-Pyrryl)acetic is added to water, the pH of which is adjusted to about 6.5 by the addition of sodium bicarbonate. This solution is cooled in an ice bath and to it is added one equivalent of 3-[[(5 methyl - 1, 3, 4-thiadiazol-2-yl) thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7-ATDCA) followed by N, N'-dicyclohexylcarbodiimide in cold dioxane. The mole ratio of (1-pyrryl) acetic acid/7-ATDCA/carbodiimide is 3/1/1. After standing overnight at ice bath temperature, the reaction mixture is filtered to remove solids. The filtrate is evaporated to dryness, the solids taken up in ethyl acetate, dried over magnesium sulfate and filtered. The ethyl acetate solution is concentrated and then treated with hexane. The title compound precipitates from solution is filtered and dried. EXAMPLE 6

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