反応 #54859

反応方程式

(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

溶媒

dioxane

water

反応条件

後処理

1. 1
   温度This solution is cooled in an ice bath and to it
2. 2
   ろ過temperature, the reaction mixture is filtered
3. 3
   その他to remove solids
4. 4
   その他The filtrate is evaporated to dryness
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮The ethyl acetate solution is concentrated
8. 8
   workup.ADDITIONtreated with hexane
9. 9
   その他The title compound precipitates from solution
10. 10
    ろ過is filtered
11. 11
    その他dried

実験手順

(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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