Fleroxacin → HCID 14781964, Verbindung

HRID 1728915

Reaktionsgleichung

Reaktionsgleichung von HRID 1728915
[O:1]=[C:2]1[N:9]2[CH:4]([S:5][CH2:6][CH:7]=[C:8]2[C:10]([OH:12])=[O:11])[CH:3]1[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:24]N([Si](C)(C)C)C(=O)C(F)(F)F.[I:36][Si](C)(C)C.[F:41][C:42]1[CH:43]=[C:44]2[C:49](=[C:50]([F:59])[C:51]=1[N:52]1[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]1)[N:48]([CH2:60][CH2:61][F:62])[CH:47]=[C:46]([C:63]([OH:65])=[O:64])[C:45]2=[O:66]>CO.C(#N)C.C(Cl)Cl>[I-:36].[C:63]([C:46]1[C:45](=[O:66])[C:44]2[C:49](=[C:50]([F:59])[C:51]([N:52]3[CH2:53][CH2:54][N+:55]([CH2:24][C:7]4[CH2:6][S:5][C@H:4]5[N:9]([C:2](=[O:1])[C@H:3]5[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:8]=4[C:10]([OH:12])=[O:11])([CH3:58])[CH2:56][CH2:57]3)=[C:42]([F:41])[CH:43]=2)[N:48]([CH2:60][CH2:61][F:62])[CH:47]=1)([OH:65])=[O:64]

Komponenten

8

Edukt 4

HCID 3357FleroxacinHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamide2×HCID 85247Trimethylsilyl iodideHCID 14286988HCID 14286988, Verbindung

Produkt 1

HCID 14781964HCID 14781964, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, a mixture of 406 mg (1 mmol) of [6R-trans]-3-(acetyloxy)methyl]-8-oxo-7-[(phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]-oct-2-en-2-carboxylic acid, 2 mL of dry methylene chloride, a nd 0.60 mL (3 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) was stirred for one hour: 0.28 mL (2 mmol) of iodotrimethylsilane was then added, and the mixture stirred for 2 hours. The solution was then concentrated to dryness under reduced pressure, and the residual oil dissolved in 2 mL of acetonitrile. Five drops of anhydrous THF were added, and the mixture was stirred for 5-10 minutes. A solution prepared from 111 mg (0.3 mmol) of 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, 0.11 mL (0.6 mmol) of MSTFA and 1 mL of acetonitrile was added, and stirring was continued for 2 hours. The mixture was chilled in ice, and approximately 100 mg of methanol were added. The solid which precipitated was filtered, washed with acetonitrile, and dried under reduced pressure to obtain the title compound: NMR (Me2SO-d6) δ 3.15 (s, 3H, NCH3), 3.45-3.85 (m, 9H, 4 x NCH2 and CH of SCH2), 3.95 (d, 1H, J gem=16.5 Hz, CH of SCH2), 4.39 and 4.77 (AB, 2H, J gem=13 Hz, NCH2). 4.61 and 4.64 (AB, 2H, J gem=15 Hz, OCH2CO), 4.83-5.07 (m, 4H, NCH2CH2F), 5.24 (d, 1H, J=5Hz, CH), 5.82 (dd, 1H, J=5 and 7 Hz, CH), 6.95 (d, 2H, J=8 Hz, Ar), 6.97 (t, 1H, J=8 Hz, Ar), 7.29 (t, 2H, J=8 Hz), 7.96 (d, 1 H, J=12 Hz, Ar), 8.91 (s, 1H, =CH--), 9.18 (d, 1H, J=7 Hz, NH); IR (KBr) 3400, 1788, 1728, 1700, 1612, cm-1 ; mass spectrum m/z 716 (cation).

Aufarbeitung

  1. concentrationThe solution was then concentrated to dryness under reduced pressure
  2. dissolutionthe residual oil dissolved in 2 mL of acetonitrile
  3. additionFive drops of anhydrous THF were added
  4. stirringthe mixture was stirred for 5-10 minutes
  5. additionwas added
  6. stirringstirring
  7. waitwas continued for 2 hours
  8. temperatureThe mixture was chilled in ice
  9. customThe solid which precipitated
  10. filtrationwas filtered
  11. washwashed with acetonitrile
  12. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5ac05a6645054790a62e5ee9c02f204a
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05329002

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