Dichloromethane → 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

HRID 839144

Reaktionsgleichung

Reaktionsgleichung von HRID 839144
ClC[C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:7]([OH:9])=O)[C:4]([OH:6])=[O:5].[CH3:16][C:17]([O:19][CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=[O:18].[CH2:34]([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[CH3:35].[CH2:41](Cl)[Cl:42]>C(O)CC>[CH2:34]([NH+:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[CH3:35].[C:17]([O:19][CH2:20][C:21]1[CH2:30][S:29][CH:24]2[N:23]([C:26](=[O:27])[CH:25]2[NH2:28])[C:22]=1[C:31]([O-:33])=[O:32])(=[O:18])[CH3:16].[C:17]([O:19][CH2:20][C:21]1[CH2:30][S:29][CH:24]2[N:23]([C:26](=[O:27])[CH:25]2[NH:28][C:7](=[O:9])[CH:3]([C:10]2[CH:11]=[CH:12][C:13]([CH2:41][Cl:42])=[CH:14][CH:15]=2)[C:4]([OH:6])=[O:5])[C:22]=1[C:31]([OH:33])=[O:32])(=[O:18])[CH3:16]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 4413287-Aminocephalosporanic acid2×HCID 53918301alpha-Chloromethylphenylmalonic acid

Produkt 2

HCID 203258543-[(Acetyloxy)-methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-carboxyacetyl]-amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 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 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

α -Carboxy-p-chloromethylphenylacetyl nitrophenyl polymer, prepared according to the procedure described in Canadian Pat. No. 892,580, carrying 4 m. mole of α-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 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 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 reamaining 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.

Aufarbeitung

  1. customprepared
  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 of distilled water
  7. additionby adding 0.2N hydrochloric acid
  8. extractionextracted twice with ethyl acetate
  9. dry with materialThe organic solution is dried over sodium sulfate
  10. customevaporated at room temperature
  11. dry with materialThe reamaining solid is dried over night over phosphorus pentoxide under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0740e2b3a1704fc0bcc6e5bd3b6f8f8e
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093804

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