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

HRID 442354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442354
[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].[C:15]([O:18][CH2:19][C:20]1[CH2:27][S:26][CH:25]2[N:22]([C:23](=[O:29])[CH:24]2[NH2:28])[C:21]=1[C:30]([OH:32])=[O:31])(=[O:17])[CH3:16]>C(OCC)(=O)C>[C:15]([O:18][CH2:19][C:20]1[CH2:27][S:26][CH:25]2[N:22]([C:23](=[O:29])[CH:24]2[NH:28][C:12](=[O:13])[CH2:11][C:8]2[CH:9]=[CH:10][C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:6][CH:7]=2)[C:21]=1[C:30]([OH:32])=[O:31])(=[O:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 20505454p-Azidomethylphenylacetyl chloride

Produkt 1

HCID 227677583-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-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 (1.38 g) and 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1.38 g) in 250 ml of ethyl acetate was refluxed for 45 minutes. The solvent was removed under vacuum at 35° C. yielding a solid residue which was purified by chromotography using 200 g of silica gel eluting with benzene-acetone to give 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. M.P. 135°-136° C.

Aufarbeitung

  1. temperaturewas refluxed for 45 minutes
  2. customThe solvent was removed under vacuum at 35° C.
  3. customyielding a solid residue which
  4. customwas purified by chromotography

Quellen und Nachweise

ORD-Eintrag
ord-740bc8cef1ae43d2834765a24ef02b09
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04045438

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