Norfloxacin → Enoxacin

HRID 373327

反応式

HRID 373327 の反応式
[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

参加物

3

反応物 2

HCID 4539NorfloxacinHCID 110826-Aminopenicillanic acid

生成物 1

HCID 3229Enoxacin収率 25%

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b084f5376e564619977ea0f5d57fc9d0
出典データセット
uspto-grants-1992_11
特許番号
US05162523

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