Norfloxacin → Enoxacin

HRID 373327

반응식

HRID 373327 반응식
[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

참가 물질

3

반응물 2

HCID 4539NorfloxacinHCID 110826-Aminopenicillanic acid

생성물 1

HCID 3229Enoxacin수율 25%

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b084f5376e564619977ea0f5d57fc9d0
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162523

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