تفاعل #2486143

معادلة التفاعل

7-aminocephalosporanic acid

triethylamine

p-chloromethylphenylmalonic acid

→

3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid triethylammonium salt

3 -[(acetyloxy)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

المذيبات

propanol

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىα-Carboxy-p-chloromethylphenylacetyl nitrophenyl polymer, prepared
2. 2
   workup.ADDITIONcontaining 1 m
3. 3
   ترشيحthe polymer is filtered off
4. 4
   غسيلwashed with 3 portions of 50 ml each of methylene chloride
5. 5
   أخرىThe combined filtrates are evaporated
6. 6
   workup.DISSOLUTIONthe residue is dissolved in 20 ml of distilled water
7. 7
   workup.ADDITIONby adding 0.2N hydrochloric acid
8. 8
   استخلاصextracted twice with ethyl acetate
9. 9
   تجفيفThe organic solution is dried over sodium sulfate
10. 10
    أخرىevaporated at room temperature
11. 11
    تجفيفThe remaining solid is dried over night over phosphorus pentoxide under vacuum

الإجراء التجريبي

α-Carboxy-p-chloromethylphenylacetyl nitrophenyl polymer, prepared according to the procedure described in Canadian Pat. No. 892,580, carrying 4 m. mole of p-chloromethylphenylmalonic acid is stirred for about 8 hours in 20 ml of dry methylene chloride solution containing 1 m. mole of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid triethylammonium salt, which is prepared from 544 mg of 7-aminocephalosporanic acid (1 m. mole) and 0.56 ml of triethylamine (1 m.mole) at room temperature. After only traces of 7-aminocephalosporanic acidremain in solution, which is determined by thin layer chromatography on cellulose in 70% aqueous propanol, the polymer is filtered off and washed with 3 portions of 50 ml each of methylene chloride. The combined filtrates are evaporated and the residue is dissolved in 20 ml of distilled water. This solution is acidified to pH 2 by adding 0.2N hydrochloric acid and extracted twice with ethyl acetate. The organic solution is dried over sodium sulfate and evaporated at room temperature. The remaining solid is dried over night over phosphorus pentoxide under vacuum to give 3 -[(acetyloxy)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

المصدر