Norfloxacin → Enoxacin

HRID 373327

Reaction equation

HRID 373327 reaction equation
[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

Participants

3

Reactant 2

HCID 4539NorfloxacinHCID 110826-Aminopenicillanic acid

Product 1

HCID 3229EnoxacinYield 25%

Procedure

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 (24.2mg, 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).

Workup

  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)

Sources & evidence

ORD record
ord-b084f5376e564619977ea0f5d57fc9d0
Source dataset
uspto-grants-1992_11
Patent number
US05162523

Linked notes

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