Reaktion #54859

Reaktionsgleichung

(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

Lösungsmittel

dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis solution is cooled in an ice bath and to it
2. 2
   Filtrationtemperature, the reaction mixture is filtered
3. 3
   Sonstigeto remove solids
4. 4
   SonstigeThe filtrate is evaporated to dryness
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   EinengenThe ethyl acetate solution is concentrated
8. 8
   workup.ADDITIONtreated with hexane
9. 9
   SonstigeThe title compound precipitates from solution
10. 10
    Filtrationis filtered
11. 11
    Sonstigedried

Vorschrift

(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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