3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl ester → 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 propionyloxymethyl ester

HRID 839150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 839150
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:13]([OH:15])=O)[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[C:16]([O:20][CH2:21][O:22][C:23]([C:25]1[N:26]2[CH:29]([S:30][CH2:31][C:32]=1[CH2:33][O:34][C:35](=[O:37])[CH3:36])[CH:28]([NH2:38])[C:27]2=[O:39])=[O:24])(=[O:19])[CH2:17][CH3:18]>C(Cl)Cl.C(O)CC>[C:16]([O:20][CH2:21][O:22][C:23]([C:25]1[N:26]2[CH:29]([S:30][CH2:31][C:32]=1[CH2:33][O:34][C:35](=[O:37])[CH3:36])[CH:28]([NH:38][C:13](=[O:15])[CH:9]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][CH:7]=1)[C:10]([OH:12])=[O:11])[C:27]2=[O:39])=[O:24])(=[O:19])[CH2:17][CH3:18]

Komponenten

5

Edukt 2

HCID 214259953-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl esterHCID 22767749p-Chloromethylphenylmalonic acid

Produkt 1

HCID 541665673-[(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 propionyloxymethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10311-PropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

α-Carboxy-p-chloromethylphenylacetylnitrophenyl polymer prepared as in the procedure of Example 22, carrying four m. mole of p-chloromethylphenylmalonic acid was suspended for about 8 hours in 20 ml of dry methylene chloride solution containing 1 millimole of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl ester. After only traces of the 7-amino-cephalosporanic acid ester derivative remain in solution, which is determined by thin layer chromatography on cellulose in 70% aqueous propanol, the polymer is filtered off and washed with portions of 50 ml each of methylene chloride. The combined filtrates are evaporated and the residue is dissolved in 20 ml of distilled water. The solution is acidified to a pH of 2 by adding 0.2 normal hydrochloric acid and extracted twice with ethylacetate. The organic solution is dried over sodium sulfate and evaporated at room temperature. The remaining solid is dried overnight 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 propionyloxymethyl ester.

Aufarbeitung

  1. customα-Carboxy-p-chloromethylphenylacetylnitrophenyl polymer prepared as in the procedure of Example 22
  2. filtrationthe polymer is filtered off
  3. washwashed with portions of 50 ml each of methylene chloride
  4. customThe combined filtrates are evaporated
  5. dissolutionthe residue is dissolved in 20 ml of distilled water
  6. additionby adding 0.2 normal hydrochloric acid
  7. extractionextracted twice with ethylacetate
  8. dry with materialThe organic solution is dried over sodium sulfate
  9. customevaporated at room temperature
  10. dry with materialThe remaining solid is dried overnight over phosphorus pentoxide under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ed1657647eae46dfa66460a1d196e378
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093804

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