تفاعل #54859

معادلة التفاعل

(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

المذيبات

dioxane

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThis solution is cooled in an ice bath and to it
2. 2
   ترشيحtemperature, the reaction mixture is filtered
3. 3
   أخرىto remove solids
4. 4
   أخرىThe filtrate is evaporated to dryness
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزThe ethyl acetate solution is concentrated
8. 8
   workup.ADDITIONtreated with hexane
9. 9
   أخرىThe title compound precipitates from solution
10. 10
    ترشيحis filtered
11. 11
    أخرىdried

الإجراء التجريبي

(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

المصدر