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

HRID 1111752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1111752
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:15]([OH:17])=O)[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH3:18][C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][C@@H:26]2[C@H:27]([NH2:30])[C:28](=[O:29])[N:25]2[C:24]=1[C:33]([OH:35])=[O:34])=[O:20].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37]>C(Cl)Cl.C(O)CC>[CH2:36]([NH+:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37].[C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][CH:26]2[N:25]([C:28](=[O:29])[CH:27]2[NH2:30])[C:24]=1[C:33]([O-:35])=[O:34])(=[O:20])[CH3:18].[C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][CH:26]2[N:25]([C:28](=[O:29])[CH:27]2[NH:30][C:15](=[O:17])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:10][CH:9]=2)[C:12]([OH:14])=[O:13])[C:24]=1[C:33]([OH:35])=[O:34])(=[O:20])[CH3:18]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 4413287-Aminocephalosporanic acid2×HCID 22767759p-Azidomethylphenylmalonic acid

Produkt 2

HCID 227677693-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)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 2

HCID 10311-PropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

α-Carboxy-p-azidomethylphenylacetyl nitrophenyl polymer, prepared according to the procedure described in Canadian Pat. No. 892,580, carrying 4 m. mole of p-azidomethyl-phenylmalonic acid was suspended for 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 was filtered off and washed with 3 portions of 5- ml each of methylene chloride. The combined filtrates were evaporated and the residue was dissolved in 20 ml of distilled water. This solution was acidified to pH 2 by adding 0.2 normal hydrochloric acid and extracted with ethyl acetate. The organic solution was dried over sodium sulfate and evaporated at room temperature. The remaining soldi was dried overnight over phosphorus pentoxide under vacuum to give 3-[ (acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8ac4a81983a74569a8f599b6cf27ea20
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04118562

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