Norfloxacin → Enoxacin

HRID 467280

Reaktionsgleichung

Reaktionsgleichung von HRID 467280
[CH3:1][CH2:2][N:3]1[C:9]2C=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]([F:14])=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1.CC1(C)S[C@@H]2[C@H](N)C(=O)[N:27]2[C@H]1C(O)=O>>[CH3:1][CH2:2][N:3]1[C:9]2[N:27]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]([F:14])=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1

Komponenten

3

Edukt 2

HCID 4539NorfloxacinHCID 110826-Aminopenicillanic acid

Produkt 1

HCID 3229EnoxacinAusbeute 25 %

Versuchsvorschrift

The tetrabutyl ammonium salt of enoxacin [J. Med. Chem., 27, 292 (1984)] was prepared and converted into the corresponding dimethylacetal, using the procedure described for the corresponding norfloxacin analog in Example 15 (but done on a 0.112 mmol scale). This was coupled to 6-aminopenicillanic acid (24. 2 mg, 0.112 mmol) by following the procedure as described for the preparation of the product in Example 33. The product, which was very unstable, was purified by preparative liquid chromatography (C-18 reverse phase, 0-100% aqueous acetonitrile gradient) to give an amorphous, pale yellow powder after lyophilization (16.4 mg, 25% yield).

Aufarbeitung

  1. customas described for the preparation of the product in Example 33
  2. customwas purified by preparative liquid chromatography (C-18 reverse phase, 0-100% aqueous acetonitrile gradient)
  3. customto give an amorphous, pale yellow powder after lyophilization (16.4 mg, 25% yield)

Quellen und Nachweise

ORD-Eintrag
ord-5fcf17405b94434099947ea0851a91fc
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05159077

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