Dicyclohexylcarbodiimide → (6R)-8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 866884

Reaktionsgleichung

Reaktionsgleichung von HRID 866884
C([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:17])[CH:15](N)[C@H:12]2[S:11][CH2:10][C:9]=1C(SC1NN=NN=1)CCNS(C)(=O)=O)=[O:7])(C)(C)C.FC(F)(F)CS(CC(O)=O)(=O)=O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[S:11]1[C@@H:12]2[CH2:15][C:14](=[O:17])[N:13]2[C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 205740432-(2,2,2-Trifluoroethanesulfonyl)acetic acidHCID 178450691HCID 178450691, Verbindung

Produkt 1

HCID 52921562(6R)-8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 9.34 g (0.019 mol) of 7-amino-3-[1-(2-methanesulfonamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid t-butyl ester and 3.9 g (0.019 mol) of 2,2,2-trifluoroethylsulfonylacetic acid in tetrahydrofuran is added dropwise a solution of 3.9 g (0.019 mol) of dicyclohexylcarbodiimide in 100 ml of tetrahydrofuran. The reaction mixture is stirred at 25° for 12 hours, then filtered and concentrated to about 10 ml. The residue is filtered and evaporated to dryness to give 7β-(2,2,2-trifluoroethylsulfonylacetamido)-3-[1-(2-methanesulfonamidoethyl)tetrazol-5-ylthiomethyl[-3-cephem-4-carboxylic acid t-butul ester.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated to about 10 ml
  3. filtrationThe residue is filtered
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ca3cedf02e9e4d02bb76f5a47687feb3
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04101656

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