Triethylamine → 3-[(2-Methyl-1,3,4-thiadiazol-5-yl-thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 839149

Reaktionsgleichung

Reaktionsgleichung von HRID 839149
ClCC1C=CC(C(C(O)=O)C(O)=O)=CC=1.CC(OCC1CS[C@@H]2[C@H](N)C(=O)N2C=1C(O)=O)=O.[CH2:34]([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[CH3:35].[CH3:41][C:42]1[S:43][C:44]([S:47][CH2:48][C:49]2[CH2:56][S:55][CH:54]3[N:51]([C:52](=[O:58])[CH:53]3[NH2:57])[C:50]=2[C:59]([OH:61])=[O:60])=[N:45][N:46]=1>C(Cl)Cl.C(O)CC>[CH2:34]([NH+:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[CH3:35].[CH3:41][C:42]1[S:43][C:44]([S:47][CH2:48][C:49]2[CH2:56][S:55][CH:54]3[N:51]([C:52](=[O:58])[CH:53]3[NH2:57])[C:50]=2[C:59]([O-:61])=[O:60])=[N:45][N:46]=1.[CH3:41][C:42]1[S:43][C:44]([S:47][CH2:48][C:49]2[CH2:56][S:55][CH:54]3[N:51]([C:52](=[O:58])[CH2:53]3)[C:50]=2[C:59]([OH:61])=[O:60])=[N:45][N:46]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 4413287-Aminocephalosporanic acidHCID 31498227-Amino-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 22767749p-Chloromethylphenylmalonic acid

Produkt 2

HCID 214366563-[(2-Methyl-1,3,4-thiadiazol-5-yl-thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 1317108003-[(2-Methyl-1,3,4-thiadiazol-5-ylthio)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-chloromethylphenylacetylnitrophenyl polymer, prepared according to the procedure described in Canadian Pat. No. 892,580, carrying 4m. mole of p-chloromethyl phenylmalonic acid is suspended for about 8 hours in 20 ml of dry methylene chloride solution containing 1 m. mole of 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid triethylammonium salt, which is prepared from the 7-aminocephalosporanic acid derivative and triethylamine at room temperature. After only traces of 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic 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 three 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 0.2 N hydrochloric acid and extracted twice with ethylacetate. The organic solution is dried over sodium sulfate and evaporated to room temperature. The remaining solid is dried overnight over phosphorus pentoxide under vacuum to give 7-[[2-[4-chloromethyl)phenyl]-2-carboxyacetyl]amino]-3-[(2-methyl-1,3,4-thiadiazol-5-yl-thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Aufarbeitung

  1. customα-Carboxy-p-chloromethylphenylacetylnitrophenyl polymer, prepared
  2. additioncontaining 1 m
  3. filtrationthe polymer is filtered off
  4. washwashed with three 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 0.2 N hydrochloric acid
  8. extractionextracted twice with ethylacetate
  9. dry with materialThe organic solution is dried over sodium sulfate
  10. customevaporated to room temperature
  11. dry with materialThe remaining solid is dried overnight over phosphorus pentoxide under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-25b52e1731714b888cc8630469c4dc66
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093804

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