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

HRID 1604918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604918
ClCC1C=CC(C(C(O)=O)C(O)=O)=CC=1.[CH2:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17].[CH3:23][C:24]([O:26][CH2:27][C:28]1[CH2:37][S:36][C@@H:31]2[C@H:32]([NH2:35])[C:33](=[O:34])[N:30]2[C:29]=1[C:38]([OH:40])=[O:39])=[O:25]>C(Cl)Cl.C(O)CC>[CH2:16]([NH+:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17].[C:24]([O:26][CH2:27][C:28]1[CH2:37][S:36][CH:31]2[N:30]([C:33](=[O:34])[CH:32]2[NH2:35])[C:29]=1[C:38]([O-:40])=[O:39])(=[O:25])[CH3:23]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 4413287-Aminocephalosporanic acidHCID 22767749p-Chloromethylphenylmalonic acid

Produkt 1

HCID 1317101243-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid triethylammonium salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10311-PropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

α-Carboxy-p-chloromethylphenylacetyl nitrophenyl polymer, prepared according to the procedure described in Canadian Patent No. 892,580, carrying 4 m. mole of p-chloromethylphenylmalonic acid is suspended 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-aminocepahlosporanic acid (1 m. mole) and 0.56 ml of triethylamine (1 m. mole) at room temperature. After only traces of 7-aminocephalosporanic acid remain 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 or 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 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.

Aufarbeitung

  1. customα-Carboxy-p-chloromethylphenylacetyl nitrophenyl polymer, prepared
  2. additioncontaining 1 m
  3. filtrationthe polymer is filtered off
  4. washwashed with 3 portions of 50 ml each of methylene chloride
  5. customThe combined filtrates are evaporated
  6. dissolutionthe residue is dissolved in 20 ml
  7. distillationdistilled water
  8. additionby adding 0.2N hydrochloric acid
  9. extractionextracted twice with ethyl acetate
  10. dry with materialThe organic solution is dried over sodium sulfate
  11. customevaporated at room temperature
  12. dry with materialThe remaining solid is dried overnight over phosphorus pentoxide under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8e08222ff9964031833b565344acf0da
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03948904

Notizen zur Reaktion

Wird geladen…