7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → 7-[[2-[4-(Azidomethyl)phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 442355

Reaktionsgleichung

Reaktionsgleichung von HRID 442355
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](Cl)=[O:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[NH2:15][CH:16]1[C:23](=[O:24])[N:22]2[CH:17]1[S:18][CH2:19][C:20]([CH3:28])=[C:21]2[C:25]([OH:27])=[O:26]>C(OCC)(=O)C>[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:15][CH:16]2[C:23](=[O:24])[N:22]3[CH:17]2[S:18][CH2:19][C:20]([CH3:28])=[C:21]3[C:25]([OH:27])=[O:26])=[O:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Komponenten

4

Edukt 2

HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 20505454p-Azidomethylphenylacetyl chloride

Produkt 1

HCID 227677437-[[2-[4-(Azidomethyl)phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of p-azidomethylphenylacetyl chloride (0.6 g) and 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (0.6 g) in 250 ml of ethyl acetate was refluxed for 50 minutes after which the solvent was removed under vacuum yielding an oily residue which was purified by chromatography using 60 g of silica gel and benzene-acetone as the eluant to give 7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. M.P. 154°-155° C.

Aufarbeitung

  1. temperaturewas refluxed for 50 minutes after which the solvent
  2. customwas removed under vacuum
  3. customyielding an oily residue which
  4. customwas purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ea0b5cbd23e419c92656ae7ae6f5b98
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04045438

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