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Levofloxacin q-acid → (3S)-10-(cis-3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid

HRID 580594
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HRID 580594 반응식
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][C@H:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[C:21]([O:25][C:26]([NH:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][NH:31][CH2:30]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>CS(C)=O>[C:21]([O:25][C:26]([NH:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][N:31]([C:3]2[C:2]([F:1])=[CH:15][C:14]3[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11][N:6]4[C@@H:7]([CH3:10])[CH2:8][O:9][C:4]=2[C:5]=34)[CH2:30]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 688333Levofloxacin q-acidHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidine

생성물 1

HCID 70419344(3S)-10-(cis-3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid수율 81.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of (3S)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid (0.5 g), anhydrous dimethyl sulfoxide (10 ml) and cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.54 g) was stirred for 2 hours at 90°-100° C. and then concentrated. The resulting residue was dissolved in chloroform and the solution was washed with 10% aqueous citric acid solution further washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The resulting precipitate was triturated in methanol and collected by filtration to give the title compound (0.67 g) as yellowish powder, mp 206°-207° C.

후처리

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in chloroform
  3. washthe solution was washed with 10% aqueous citric acid solution
  4. washfurther washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting precipitate was triturated in methanol
  8. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-83b4e378ac2346d19bd5dadc5e979196
출처 데이터셋
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04753953

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